What makes a self-directed IRA custodian different is that they are not purely connected to the public exchanges and limited to investing in stocks, bonds and funds, but rather have the staff training and paperwork to document the IRA's investment in the more individualized transactions that occur when investing in real estate, notes and other non-traditional assets.

Given you are in Milwaukee where I would assume home prices are still reasonable, you could buy 5 rental properties that would cash flow ~$250 a month each or an extra $15,000 a year total.

I lease the rooms individually to veterans.

If you're looking for a house hack I would wait patiently for the right 2-4 unit that works well for you and your own individual needs or I would buy an older SFH with an accessory dwelling unit (or the opportunity to add your own or convert an unused structure on the property).

Cap rate is a function of market risk and rarely will change on individual properties. 

I have a park with some extra land, I can explore this idea too. 

What I want to know is what banks have individuals had the best experience with down in south florida.

Should I ask the bank for an extra amount (maybe 1.5x my estimated repair costs) to cover for incidentals? 

Additionally, If your city does not have their own individual ADU compliance rules signed into law and regulations by Jan 01, 2020 they must default to the state rules with no additional requirements.John, my understanding was similar to yours regarding parking, the property I just purchased in Anaheim with detached garage is less then .5 miles from public transportation, yet my initial ADU report from Hausable states I need one covered parking spot.  

Cost segregation combined with bonus depreciation is huge.A lot easier to 1031 one 100 unit property than 100 individual houses.Apartment rehab often stays below the $2500 de minimis safe harbor per item (because apartment communities don't pay retail) - which means immediate deduction and no future depreciation recapture (i.e. an HVAC replacement may only cost $2400).Some apartment rehab above $2500 per item can be immediately deducted if it does not meet the 20% "unit of property" rules (i.e. replace one HVAC system in a ten unit building).