@Akshay BhaskaranI hate to sound negative, but your proposal has “victim” written all over it to me at almost every turn.

(this means the market rents will be more than PITI)Use proposed/current rents to qualify for the largest property possible. 

Cap Rate is low, and a big maintenance task would put this in the negatives quickly, but I'm hoping since it's a recent flip that those will be minimized, but you never truly know that for sure. in my mind based on the financing U propose as long as it does not bleed u your bound to do well on it over the years with rising rents and subsequent value rise when rents go up..

"After you've done a couple hundred deals, you'll find that objections or questions arise not from a proposed buyer but by third parties who are in some position of influence with that buyer.

Of course, these are assumptions here, but wondering what the experienced investor would propose in this situation, with the current funds in the current market, with the current strategy.TIA!

Just need to verify that the rents will cover the proposed mortgage payment and FICO score. 

I am not a fan of being far from my STRs, and I bought one of my buildings from someone in North Ireland who was tired of being somewhat helpless being so far removed from his place.I would suggest you run your proposed property and area through mashvisor, airdna, Airbnb, VRBO to get an idea.

The proposal was for a lottery.  

They need to both 1) like the use being proposed and 2) not deem the use incompatible with their adopted general plan among myriad other issues ranging from environmental to biological, etc.

It seems like a lot of people start with dreams of a vacation home and then run into many of the challenges you noted.I'll propose an alternate idea for you.