The two key factors that helped me close on that deal were 1) a group of folks that I relied on and 2) numbers.

The main point is to find distressed properties to get the biggest discount possible.

@Jacob D AdamczakThere is no one right answer and a lot of other factors beyond just the simple one at hand come into play - age, other savings, goals, time you expect to be with this employer, etc.That company match paired with the tax deduction you get on your own contribution are essentially free and immediate return on investment. 

Nevertheless, the rehab should help improve rents, depending on other factors.

Not having access to these (which the owner in the scenario DOES enjoy) leaves you with cashflow - but with very little in the way of knobs, dials and levers with which to manipulate the factors that influence cashflow... 

I think that area is going to do well with the new complex’s going in at 5th and Main. 

Yes, people are still using Airbnb but if you are basing your main long term investment around it I would really consider other exit strategies and alternative monetization

I deal with mainly higher end units which get phenominal cash flow, but the problem is there isn't a lot of good comparable data.

@Alina Trigub I mainly work with web applications.

Obviously there is a lot of factors left out of this (will bank approve, you name another etc) but just from a theoretical standpoint is what I proposed (using tenants $300K down payment as a down payment for my traditional loan) illegal or just not feasible and I've completely missed something here that more experienced people can explain to me when they are done having their chuckle.