Many members are experts in their respective fields related to real estate investing, whether that is real estate brokerage, wholesaling, flipping, buy and hold, lending, self-directed IRA and Solo 401k investing, or tax and legal guidance.There are some pretty cool discounts on various products and services offered as Perks to BP members that you might want to check out: https://www.biggerpockets.com/perks/pro

First, Chicago is extremely tenant friendly, so if you are investing in C or D areas which can only attract poorer credit, lower income or subsidized tenants, you WILL (I promise) have problems with getting all your money, property maintenance, and lost rents.

Keep in mind the characteristics of these types of loan products (balloon payments, etc.). 

Any other advice would be extremely apprieciated!

I am thinking your product is on the high side of that since you deal in the top part of the SFR rental space.. when your not doing apartments.

Ours is in an area that is primarily summer only but with continuous improvements and a good rental manager our utilization is increasing into spring and fall.Best part about vacation Rentals, no concerns about evictions.Worst part, extremely hard to cash flow with traditional LTV rates.

But the 1031 is only available when your intent in purchasing a property has been to hold for productive use (like you do with your long term rentals).There is no specific holding period. 

A by product, yes, but not your why.

A little more informationL Our HML didn’t want us to owner occupy, as it still was a non-owner occupied product, but had no problem lending to us in our own names, with no entity involved.

Tampa, FL:I am extremely new to buying property.