Some people are more disturbed by that than others (even if they have nothing to hide) - and following you around may give them a greater sense of control and therefore comfort.

What price range are you comfortable with?

Or if your'e living in it would you feel comfortable in that area. 

For real estate just start analyzing as many deals as you can so you get more comfortable and confident.

Quote from @Michael Challenger: I have no qualms with hard money lending, but I need to learn more about the process and structure to these for typical deals so that I am more comfortable and in a position to reduce my personal risk and risk to investors as much as possible.

Plenty of people invest remotely, and as long as you have modest expectations (not chasing the highest possible yield), and are using light leverage, and don't get suckered into buying in a part of town that you wouldn't feel comfortable visiting in broad daylight, plenty of people do this and do... fine.

This will give you clarity on the numbers and help you determine how to structure an offer that works for both sides.

I think you should also confirm to them what lease renewal terms you are offering them so they can make an informed decision.If you make the repairs, you'll create some goodwill with the tenant and they will be more likely to renew.

- How many below-asking price offers will they write for you before ignoring you?

Also review what others offer.