That gives me a nice buffer.The house I would be buying is 3500+ Sq ft just about one block away from a college.

I think it can be a good starting block if there is cashflow.

So I’ve since blocked off the third floor on one side and rented it as a 1 BR for now. but when the other side leaves eventually I’m starting to lean towards raising the ground grade 28” so that the total drop is less than 20’and then I’ll knock down some walls and make the whole 3rd floor attached only to that last unit so that the whole area can use the stairs and that window as second egress. 

Haha Hey @Jacob Pereira Sorry to get your hopes up - I spoke without thinking in my excitement to talk about 1031s and skipped over a crucial stumbling block for your dream strategy ;) Allow me to clarify:So, if you live in one side of the duplex for two years within the five years prior to the sale, then it is considered residence use.

Purchase price: $88,000 Cash invested: $44,811 Sale price: $190,000 1 bed 1 bath 3rd floor walk-up just a block from the lake in Roger's Park.

The facility was built in the 1980's, cinder block construction, and needs complete rehab... 

Making sure the property "flows" outside is a key component I have personally found - assuring nobody is stepping on toes, encroaching on each other's outside space, or blocking cars in, etc. 

The annual nature of tax benefits.One of the fundamental building blocks of our tax system is its annual focus.

Just last week, I tried going to my calendar on Airbnb for next summer to look at pricing, and the calendars on all platforms were blocked from Jan 1st on. 

If you ever plan on doing this later in your days, you could always do a management company and just expand on that, but I can tell you from my own perspective  that LLC – S and being W2 employee under that may limit some of your lending aspects, but it protects you around the world anywhere you go further if it comes to it, you can bankrupt your company, sell the assets and open another company the same way and you’re still protected through and through. as my wife is a high earner, it really protects her from civil suits and other things like that or anybody that ever comes to maliciously take what is yours.