I guess it depends on if you think home prices will continue to go up over the next two years or not.  

Depending on what type of relationship you have with your lender you can have them disapprove the loan to protect your EMD. 3.

Both lead to that buyer overpaying and taking an opportunity off the board for the investors who have their underwriting completed accurately.I believe its somewhat market dependent but it has become increasingly difficult to make construction oriented deals work in the price points you mentioned.

I guess it depends on where you are buying.

Rates for STR management typically range from 20-30% of revenue, depending on the level of service and market demand

(Making judgements based on family status, number of kids, medical animals, etc etc..)4) When you get that first repair call 10pm Saturday night for a leaking roof or water heater do you have a trusted/dependable guy to call and get it fixed that night?

But rents are usually 25-100% more than market rate depending on proximity to bars, campus, etc. 

Depending on the tenant and what their financial situation is, you might also be better off giving them a 60 day notice and just telling them that you're planning to move into the property and do some updating. 30 days is usually too short for someone to have to move on, 60 days is plenty of notice for them to be able to pack and find another place.

You will have to pay for an appraisal to and depending on what the value is it will be up to you to determine if you want to proceed or not. 

Then it will go to tax sale and typically back to the county.The mortgage company could try and repair the property to protect their asset but it depends.