I recently acquired my first primary residence and am seeing ways I can best utilize the space for real estate investing.

I have also utilized owner financing for longer periods of time, including personal residence and 2 barrier island houses on the coast of Florida.  

(To avoid months of probate and thousands if not $10’s of thousands of dollars in costs.)Hawaii is considered a "TOD deed state," meaning that residents can utilize Transfer on Death (TOD) deeds to designate beneficiaries who will inherit their property upon their death, allowing for a potential bypass of probate court proceedings.If she is already in memory care center.

Quote from @Elisabeth Lernhardt: Today I found out, that some of the utilities were not in the tenants name!

ALTA survey, utility survey, etc.$100k per building, I'd say not usually. 

The down side is that STRs are more work, need to furnish it, pay for utilities and WiFI but in the right market (vacationers and business travelers) it could work. - If I were looking at cash flow as a really important important metric, I'd consider starting a business.

I purchased a home 2.5 years ago utilizing the New York First Homebuyers Club which gives you approximately 8k in grants if you meet certain criteria, which I did.

Since I was only filing on major things like underground utilities, fires, etc.

You're on a great track - best of luck and definitely utilize BP as much as possible! 

I would count on having at least half market rate tenants, in the event Section 8 rents are higher than market, which they are in our market (granted you will need to subtract the utilities from the rent).