Also, my current CPA (who also resides in Chicago) is great and also specializes in real estate.I will add that spending the necessary money on a solid CPA is worth its weight in gold and pulling the trigger before you feel like you can afford it is a good thing!

The longer you're in the business, the more weight you'll carry - but ONLY if you know what you're doing.

It is important to look at the HOA's reserve funds, and look at their meeting minutes to discuss upcoming repairs, etc, and how they tend to upkeep the community.  

Thank you all for this forum, its upkeep and dialog.I am looking into building relationships with like minded individuals who can provide me with information that I can use to put all the RE pieces together. 

I am however very familiar with cosmetic renovations in value add type deals, but I usually wind up keeping them as rentals because they're in good neighborhoods with a good tenant pool.

They sell it by weight. 

I would be lying if I said I haven’t done the same thing with making a service call from my bed lol…I also self manage and although I do agree that a big part of property management is service call related…but a great PM will go the extra mile when placing tenants, upkeep of the property, organization with financials ect… 

As for the property management quote, I wouldn’t put a lot of weight in that unless you are going to use property management. 

I am certainly one of the bigger proponents of STR's, but I do think it is important to keep in mind that these are assets which require creativity, upkeep, costs, and a whole lot of TLC.

The figures in the example are strictly to explain the strategy, please don't put too much weight on it.There is a cancellation clause in the contract that protects the home owner and contractor.