If there are any helpful answers, I believe such responses would also be valuable to others in my position.Thank You! 

I've spoken to 7 agents here in California and none are really knowledgeable about str friendly hoas, they ask send me the canned responses at this point I've accumulated 100 percent legal strs in different counties in California.

You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

@Kyle Kulhanek To retitle your Chicago condo into an LLC for liability protection, start by forming the LLC with a clear operating agreement outlining ownership and responsibilities.

I have properties in the Buffalo area (a mix of long term and short term) but was looking into Syracuse also, so would be interested to hear the responses.  

Matt Scott, Incite Venture Capital and his team can be summarized as follows: over priced, non responsive, non professional agreement breaking, chip on their shoulder and otherwise a bad investment.

Some of them even walk off the job, even after they pull permits and are technically responsible for the work.  

I'm lucky to have a motivated client/investor that wants to work with me, and I feel a tremendous amount of responsibility to take care of that trust and investment.

I invite seasoned investors to share their experience buying their first 2-4 unit properties. here are some questions to base your response/story1) how did you find your first property ?

This is where I would focus, as these are the same attributes that attracted those responsible for the larger projects like the Bellweather District you mentioned in your initial post.With your budget I would recommend NW Philadelphia (Germantown and Mount Airy in particular).