The max loan amount is $625,000 (I will need to bring $88,000 to close)  This will eat up nearly all my cash but I will get the better rate and a lock for 12 months, plus the peace of mind of a one time closing.  2nd option is a Jumbo construction loan to perm.  

I know that someday I want a peaceful house surrounded by nature, but beyond that I'm not too sure.

Although you are right as far as getting top rent for the open market we are still in a pandemic so even that isnt guaranteed atleast with Section 8 I have peace of mind knowing that I am cash flowing.

That doesn't account for the peace of mind knowing that a property is paid off, which you can't assign a $ value to.

And it is in your best interest to keep the peace and be seen as a resource and problem solver to your tenant.

While the paperwork can be a pain, it is something you could do on your own with a little research into the matter but an attorney wouldn't be that expensive to set you up with it for peace of mind.

What have you learned in placing tenants, and what sort of extra lease features/common sense did you do to keep the peace?

I am 73 and I just sold my last house in Tampa for Cash and moved to the peace and quiet of a gated Townhome in Valrico. 

Also, the inspection for a condo will be much cheaper and shorter than a single-family or multi, so it's worth the peace of mind.

How much you keep is up to you, but I don't have a high W-2, so I make up for it in reserves that could cover major expenses (enough to replace roofs on several properties at once) That's for my peace of mind being a single parent running a business.