It's not hard to find people involved in real estate who are older than me.

Speak with a commercial insurance professional that works with real estate investors.They'll know more than anyone here!

I'd be able to make a couple of hundred a month that way, but I lose a lot of tax benefits.My preference is a lease option, but I'm struggling to price this out.

There are dozens of good books out there that will give you a basic overview but based on your description of skills/assets you will probably learn little more than you already know from your own experience. 

It'll probably be a couple more years because I keep going to other more lucrative short term projects, but I'll get there eventually. 

Also, you can seek an exception from most DSCR lenders and they get approved at a high rate, it will just come with an increased origination fee (usually .5% for exceptions) or a interest rate add on. 

Real estate overall is slower during winter than summer.

Im focused mostly on the permanent financing part of the equation and dont currently offer hard money/ABL lending products, but I'm more than happy to connect you with everyone.

Also, consider making the first photo something more exciting than twin beds.

Because they are a professionally licensed business, a judge will hold them more accountable than you.