Quote from @Chris Seveney: @Charlene Kingsnorth have you had an sec attorney also review what you are doing as if you're are having multiple people as part of a loan participating in it depending on the state this could get you in hot water - so be careful  good point Chris some state allow fractionalized deed of Trust mortgages other do not or require PPM like documents prior to offering them..

Working this backwards, what I see is a 3rd party trying to benefit from another’s house via rental cashflow, My only business is 30+ years as probate estate and trust lending in CA.

Sure.Do you have a wealthy uncle that trusts you that would loan you 100% of the funds PLUS closing costs? 

- If so, 1031 into something bigger and easier to manage and then when you pass, the inheritor receives your property(s) at a stepped up basis - subject to Inheritance Tax limits.Otherwise, sell one every 1-5 years when you need the cash, so you can plan expenses to offset capital gains.14 properties - presume these had to have been single families.Oh, I'm modifying the original post to mention leaning toward creating a trust which we manage..so we would own very little yet manage the trust which owned investments and such.Here is what I understand/misunderstand (better or worse) on moving every 2 years (as we are open to that albeit pia.) • Multi-unit would only support a %, so a quad would 25% and prorated over all years of ownership....witteling advantage to not worth the effort. • Single unit properties get pro-rated.

Don’t focus on buying or selling right away—just connect and build trust.Both brokers and sellers prefer doing business with those they know and trust.

In order to have checkbook control, the IRA account will need to be at a trust company that will allow the IRA to invest in an LLC (where you will be the manager and your IRA will be member - an as manager you will have checkbook access to the LLC bank account).

Talk to a tax advisor that you trust or know someone personally that has high trust with them.  

1099, social security, trust payments, annuities, etc?

This means you need to pad your rehab costs, make sure you have trusted service providers that do great work, and when you run comps be sure to bring them down a bit and see if the deal still makes sense. 

No question is too silly, trust me, I’ve asked them all.