You should be able to get a good feel for their knowledge and expertise through digital resources they provide (webinars, youtube videos, social content) Character - You need to believe they have your best in mind and they prioritize it.

I would offer it on a land contract to someone wanting to live there for around 1500 and small down payment or sub2 with a large down payment and monthly that would cover PITI.

So she's just behind in her mortgage and probably has a notice of default or whatever the procedure is in Florida.Your ability to get a loan for the home has nothing to do with her payment history on the home.  

Attractive digital marketing fliers, 3d tours, professional tours, rent specials, and competitive pricing all help too!

He was playing nice, but then started to really press me about the final payment which was a large sum of money.

If it is accrual, then when you actually make the payment does not matter.  

He took a 401(k) loan to fund the down payment on a four-unit building in a rapidly appreciating neighborhood.

After they asses what all needs replacing or what they feel needs replacing they'll submit to you what they're willing to cover and deductibles and payments etc. 

Publication 15, Employer's Tax Guide, says only this much:...Payments for the services of a child under age 18 who works for their parent in a trade or business aren't subject to social security andMedicare taxes...No definition, and IRS publications are not really law anyway.

My PMLs are people with self-directed IRA who are perfectly fine with 5-year term while earning double-digit returns passively tax-free in their SDIRA.