I never looked to the Future for Retirement I was mostly concerned with just riding my motorcycles going to work to pay some bills and just ride like I have been doing for over 35yrs.Well that almost came to an end last year when someone decided to run a Red Light Late I T-Boned a Truck on my motorcycle on my way to work and am lucky to be alive to type today.To make a long story short I am getting a Settlement enough to buy a home cash if I want but looking to invest in Rental property to help supplement Retirement.

I am just a College biology professor who is now a small-time RE investor to supplement my meager teacher's pension.

Assumption buyers can often get a supplemental (think: second mortgage) but those carry higher rates so the buyer still needs a discount. 

Hey Mark - In my analyses, if I rented out both units I'd receive a negative cash flow of around $200/month.If I lived in one unit the cash flow would be worse, but the rented unit would still supplement my living costs.You're right, the prospect of positive cash flow may get better down the road if I rent both units and rent appreciates in my market. 

I'm looking into Real Estate for a couple of different reasons: I want to supplement my current income in homes of "retiring early" and doing Real Estate full time as I'm very interested in it, I find Real Estate much more interesting and exciting than the Stock Market, and lastly, I would like to get involved in something more personable hands-on in my spare time. 

Will it cash flow with you living there, or just supplement your mortgage payment and expenses a bit?

I see 3 issues, financial, emotional, professional :Financial - The CARES act has provided unemployment benefits and supplements on top mostly.

And then extended to 'how will I supplement retirement?'. 

@Will Fraser I’ve dabbled with the idea of focusing on a VRBO property to supplement my cash flow issue.

Recently I’ve been catch a ton of flack on this forum for suggesting things like:1) Maximizing leverage while carrying hefty reserves.2) Buying for appreciation in western markets.3) Buying properties that barely cash flow (for appreciation) and following each up with a STR to supplement cash flow.I feel like the general vibe is hesitation.