Initially I started with a single family and scaled to multi family.

This seems like an odd strategy - purposefully invest in an asset that loses value, with the hope that it will regain value (so you at least get your initial investment back) all to save a little on taxes. 

In Vermont, LLC formation fees and annual report costs can add up.A good friend of mine, Jason, started with five doors and used a single LLC for his properties initially.

Not exactly sure about the legal details, but initial overview of the system seems to suggest this kills quite a few birds with one stone.  

Areas like Aurora, Arvada, and parts of Lakewood or Westminster can be good places to look, depending on your budget and target tenant.If you’re looking for a base hit rather than a home run, focus on finding a property where the numbers work reasonably well as-is—cash flow might not be huge initially, but if you’ve got room to add value and refinance, you’ll build equity to reinvest.

You can initiate an auction or wait for ones to pop up that have been initiated by others.

Actually, you were on the right track initially.

The cost of the right advisor initially is a lot less in the long when you pick a bad advisor.

My initial idea was to find a house in the &150k-$200k range and flip it for $300k-&350k.

 - a study on rent cost compared to ownership cost shows that virtually every large city market it is initially cheaper to rent than own (I believe is was cheaper to went in 97 of the largest 100 markets)Miami and Florida have extra concerns:- insurance difficulties have resulted in large increase in insurance costs.