I'm currently living in Crown Point Indiana and hope to invest in surrounding Northwest Indiana (Hobart, Merrillville, Portage, Lake Station) and maybe eventually the South West suburbs of Chicago.I'm mostly interested in flipping single family homes and purchasing smaller multi families. 

For the first 12 months only 25% of the debt is counted towards the DTI, after 12 months none of it counts towards their DTI.If someone is desperate enough to sell their home sub-to, chances are good that they aren't buying a new property within a year anyway.

They apparently have strict rules about what the owner company can be involved with. 

Here’s my situation: I currently own a home the vacation destination New Smyrna Beach, Florida.

I am interested in adding a 264 sq feet space in my front yard, attached to the main home for rental purpose.

This is not a financial planning question but a simple can you afford to buy a home and how much can you afford if you can buy.You might have better luck posting in the home buying section of this site as this personal finance portion of BP doesn't get much attention.

@Adam Eckhoff I personally prefer real estate over stocks because it gives a quicker return on cash in your pocket (unless you are a skilled day trader/options trader).

Mike,If you are not going to cover your belongings and the parts of the Building you ar responsible for, another avenue to try is to see if your Homeowners policy can add that location for Liability only.  

The home is worth $1.3mm today, and I have $700k remaining mortgage and $600k equity in the house.

I also suspect home prices would initially rise on the first 1-1.5% of cuts, but ultimately fall once we get to the 3-4% range as large  pre-pandemic supply comes back online, compounded by boomer land lords selling realizing the top of the market is in the rear view mirror (at least for them).If you eventually get squeezed on lower rents and valuations as the market normalizes, the ability to BRRR your pandemic era deals will be limited, so how do avoid trapping capital in the deals you already own from this environment?