Short Sales have been very good to me but I only select the ones that make it worth my while.

True here in FL as well, unless you select "present only written offers" on the listing agreement, which is standard operating procedure for my broker. 

To specifically address your point #4 in your post, check out a Company called Polser USA which has a patented FRP product currently used in RV’s that has been clinically proven to kill micro organisms and is chemical free.

They chose to select it during their search and sign a lease to live in your property without central a/c and if they seem happy with it, perhaps you should let sleeping dogs lie Originally posted by @Steele Evans:@Bradley Padula You are right, 4 years seems like a long time to recoup that expense. . 

Within your search/selections, I can provide rental history and projections and often P&L to include annual expenses (flood, wind, and hail insurance).

If you rent it for more than 3 years, you will lose the capital gain tax exclusion on the sale of a primary residence (google sec 121 exclusion).Many of us would not select either of your choices but would use the proceeds to invest in real estate.

I know there is a lot of information out there but if someone can point me to a simple step wise guidance as to what to look for from site selection (like what questions to ask etc) all the way to get into thick of actual development, I will be greatly obliged.

My main question is, if I don’t plan to do a tremendous amount of work in the new property, but I am willing to do some cosmetic upgrades, does it feel safer to buy something that’s already occupied and has good tenant history… Or some thing on occupied where I can be sure tenant selection is stringent?

Your earnest money deposit should be held by your title company in escrow until closing or termination of the contract.The buyer has the option/right to select the title company unless it is an attorney state, in which case the buyer's attny would select who will do the title work.That being said, until you know the ropes a bit more, the earlier suggestion about speaking with a competent real estate attorney is valuable advice as per @Nicole Holcomb. 

Visit the BP rental calculator at https://www.biggerpockets.com/...You can click that link, or go to the "Tools" menu on BP, and under "Calculators", select "Rental Property".