I find TPs rent control too restrictive personally.

The HELOC would need to go off your personal situation but if needed you may be able to do DSCR on the short term rental.

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

i would say it depends on the overall investment strategy. im not really familiar with STR rentals in your area. personally i like the long term rentals, especially if you are trying to be hands off. we have two STR's, one we manage ourselves in FL and the other in Gatlingburg which is managed by a company. even with an STR rental company, i still find myself managing the manager. both require work and are by no means passive. long term (to me) is nice given time investment. hope this helps. 

I personally would use Shane Flipping- Flipping Custom Homes. 

Personally, I'd be very conservative in my revenue projections on something like this just in case this trend continues. 

why no MLS  agents may have done a bunch of your homework up front.. just offer what makes sense to you.. me personally I would start with  the zoning maps and only look at props zoned for the size you want to create.. then work backwards.. no sense chasing deals without knowing the zoning up front.

You need to compare your cost of living, and overall personal cashflow each money with your current situation vs. this potential new acquisition.

Yes you can use zillow/apartments.com/Craiglist, but the most success i have personally would be FB Market place.

I’m not a greedy person in the least bit.