The key is in the interpretation of the passive income rules and guidelines which define what is a REP (real estate professional), as it relates to this space.I am looking for:1.

@Darian Gore Here are the things that many CPAs support their clients with:Understanding tax impact of short-term vs. long-term vs. flip before you buyWhich entity structure is best for goals and investment property typeTax and compliance on LLC or S-CorpHow to transfer property out of personal name into LLC (hard to buy 1st through entity)Ways to optimize taxes throughout the yearHow best to set up accounting to track income and expenses (doing this late is a mess)Feedback on property management systems, accounting systems. systems, etcEstimated payments to avoid penaltiesKnowing when to file and getting things in on timeMaybe a few things I missed, but this is the high-level ….. if you can get answers to the above questions on your own, plan, and file your own taxes then you can avoid the expense of a CPA.

Income Flow: Is it feasible to have the rental income flow to the family member, akin to purchasing an annuity, thus providing them with a steady income stream?

All income and expenses will be handled by the LLC.

Your debt to income ratio (DTI) must be below 40% (depends on the mortgage company).

The best strategies for any type of cash flow are coliving/rent by the room (would recommend Homeroom for a passive hands off turnkey type investment that still will produce income), multi-family 2-4 units where a rehab/value add is needed, or buying a property with an ADU/Guest house and treating each unit separate unit. 

Is there a certain amount of income you have to make to be qualified? 

If they continue to rent out my properties that's a really nice income for them. 

I have it advertised to rent now and I've got someone who is potentially interested in purchasing the house outright or doing a lease option. my questions are:1.) if I sell it out right, only having owned it for 4 months will I get slammed with self employment tax and regular income tax and not be eligible for 1031 exchange. or could I still call it an investment property and be able to 1031 because my intent was to rent it?

1) Primary home - GA - titled to me - Trust or LLC or both2) Secondary home - GA - titled to spouse - Trust or LLC or both3) Rental property - GA - titled to me - 4) Savings/CD Accounts - 1M - GA 5) W2 income  (self and spouse)Thanks,Vidit