My target market is the construction industry and I have been a VA for over five (5) years.
It sounds as if your potential client is an owner, maybe of rental property (?), and not a general contractor, from the way you have phrased your questions.
Some basic info - a general contractor will hire sub-contractors to perform specific tasks that the general contractor has asked the sub-contractors to bid on. Normally the agreement (or contract) between the general contractor and sub-contractor will state the quality of work being done. The general contractor will then inspect the work prior to paying the subcontractor for the work. Should the general contractor question the quality of work performed by the sub-contractor, then a discussion will follow (I will not outline all of the possible scenarios that could occur).
1.) Ensure, from a remote location, that contractors are doing the work and doing it well---> Okay, so before and after pictures? How do I ensure the date? Ask them to Skype me? A lot of contractors don't carry smartphones as they break too easily on the job.
From my experience, most sub-contractors and even general contractors use smartphones or phones/tablets that are capable of taking pictures and sending messages. If the sub-contractor or general contractor is not using a smartphone, they probably also are not familiar with Skype.
One of my clients will take pictures while on the job and send them to me via text message (to my smartphone). This is usually because the job has unknown issues and my client wants to show what occurred on that job. I can then send the before and after pictures to their client with their invoice. Normally I will add a note or comment on the invoice that pictures were taken while at the job site and are being sent with the invoice.
There is no way to "ensure from a remote location that contractors are doing the work and doing it well". If you are not familiar with how a particular task is to be done, there is no way you can ensure from a remote location that it is being done well or correctly. All you are able to do is get documentation that the work was being done. I would never agree to ensure, from a remote location or on site, that the contractors are doing the work and doing it well. I do not have that experience and I have been working in the construction industry for over fifteen years. I also worked with owners of investment/rental property on property that was gutted to the studs and renovated. While I meet with the various building inspectors (to save the owners having the sub-contractors bill them for waiting for the inspectors to show up), I never stated the condition of the work. Of course, there were items that I was familiar with over time and I could advise the owner of my opinion of the sub-contractor's work (usually after a failed inspection with the City inspector), I would never agree to "ensure from a remote location that contractors are doing the work and doing it well".
2.) On the property there are several street lights. The often need to be replaced, however, we do not have any current way of knowing which ones were replaced / when, and which may be under warrantee and we should not have to pay for them. If we hired you, what system would you put into place to ensure we never paid for a light repair that was covered under warrantee?---> Keeping track of this would be no problem, but how would I initially learn which ones might be under warranty with no prior information?
I do not understand why street lights would need to be replaced often. Are people damaging them or are the bulbs burning out? In my contracts for my clients, I specifically state what information that I would need to perform their tasks. Here I would ask for any and all information regarding the installation and repair of streets lights on (property address). Unless you are provided with the information from your potential client, there is no way that you will be able to ascertain which street lights are under warranty. You may also want to research who is responsible for "street lights" in that area, if the "street lights" were installed by a locality, they may be on an easement and there may be rules in effect for maintenance and repair of the street lights.
3.) What questions would I ask about an attached bill for a drain replacement? --> This is pretty straightforward, right? Just ask what was wrong with the drain, how they repaired it, and then research the cheapest ways that can be repaired, so we know we aren't being charged an inflated price?
After an owner has contracted with someone to do the repair, the invoice or bill from the sub-contractor is to be paid and not questioned unless the invoice price differs from the quoted price. The time to research the "cheapest way" for the repair is before the sub-contractor does the work. A word of advice, just because the quote is the "cheapest way" doesn't mean that the work was done in a reasonable workmanlike manner. There are shortcuts that sub-contractors can take so that they are the lowest bidder on the job, or the quote does not list something that is required for the job but because it was not on the quote and you did not know that it was necessary you will have to pay more for that something.
As to what tools of communication that I use between my clients, it depends on my client. I use e-mail, phone and text messages for communication between my clients.
One of my clients has their employees clock in and out on their smartphones. I then create the Payroll summary and send it to my client for their review before I create Payroll checks. I use a mix of "old" and "new" school time-tracking for my clients. The main reason is that it is easier for me to write down on a "timesheet" (designed by me for each client) what I was done for each client. I then enter some of the information from the "timesheet" into QuickBooks (single time entry). After I have posted the "timesheet" to QuickBooks, I scan the "timesheet" and it is filed digitally by client. I do this should a client a question an entry(ies) on an invoice, I am able to quickly go back to my notes for that time entry and answer my client's question.
I also use Dropbox for most of the documents that need to be sent to my clients. That way they can quickly find a document that I have created without having to search their inbox to find an e-mail from me regarding that document.
I hope that this helps you.