We used Stessa for the flips last year, but as I've increased the number of flips, tying expenses to the appropriate project has become a bear and I'm wondering what others do. 

Back of the napkin, if I were to look at your situation, I'd want to see if there would be quick ways to get increase your credit score. 

As an example, if you were to increase it up to 60 reviews in the past 12 months, then you would be left on the map with a small number of listings, all of them with a high number of bookings throughout the year.This number is a parameter in the model that users can adjust at any time.

This will increase the return above what can be obtained on a passive investment.The flipside of having the power to control everything is that it can be alot of work (and a full-time job if a person is putting in sweat equity).

Last comment, if you are using the pricing guides from CMHA as your rent standard, that would be if fair market rent comparisons are available and you pay for everything. 

It sounds like your finances are tight as a young professional with a family, I'd advice work on increasing your W2 income, with more education or training.

I have seen 20 unit properties on the MLS with a standard agent that is selling single family homes, and I have seen 6 units on Loopnet with brokers that only focus exclusively on (fill in the threshold) type listing.  

I'm wondering if some existing owners are getting out of short-term rentals because of the numbers, which would further reduce supply and, the thinking goes, increase revPAR/occupancy.) 

(I could probably get this increased but I'd have to get primary residence Sq ft re-evaluated since the basement is finished and heated but of course thay would increase my property taxes.)Thinking about refinancing primary residence and taking money out to do the additional building. 

so most people will have to be as leveraged as possible to scale (at the beginning). as in, keep your LTV high and focus on buying 'as much' ($$) RE as possible. this is if you're doing a pretty run of the mill REI strategy like buy and hold. i came across an interesting guideline once: if you could sell today and net 7x+ your annual true net cashflow, you should cash-out/refi, or sell/1031. think of it this way: if your portfolio in a year is worth 1m market value, and you owe 600k, and have a lender that will do a portfolio loan at 80% ltv, you could cashout refi and get 200k to play with (minus closing costs). when you compare the now-lower cashflow from the existing portfolio (higher LTV & maybe different rate), to what you can do with 200k cash, THAT'S where it gets fun. maybe you lose 1k/mo in cashflow on the original portfolio (literally just made up a number, idk), but you can gain 2500/mo in cashflow with that 200k.. then doing the cashout/refi earned you a net increase in your monthly profit of 1500/mo, plus you're getting debt paydown and appreciation on "more" real estate, probably getting bigger tax benefits, etc.