Hey Jason, Luckily haven't had to apply for the assistance for my own tenants, but have been helping clients with this and yes it's been a pain.

If this is your only property, a CPA might be able to help you better decide whether 2 entities are better than 1 - comparing the tax implications and administrative burden.  

I am hoping to do solar panels, my current property will need a new roof soon and I would like to do something like the tesla solar roof to knock out two birds with one stone, Hopefully the new administration will create some more incentives for solar that we can take advantage of. 

You can then charge a complimentary administration/move-in fee.

if the later, that's not going to be kosher.as a fellow bay area resident I feel your pain. have you considered moving from flips to BRRR -- if you hold the property for at least 1 year then you will be taxed via long-term capital gains. so basically you rent the place out for a year after the rehab, collect the rent and then sell. but since you've refinanced after the rehab you get much of your money back out. then you can 1031 exchange the purchase of your next property and defer the gains...I'm no CPA, but if you're interested in doing projects that involve longer holding periods and it's your primary form of income you may be eligible for real estate professional status which has huge tax benefits 

I'm done with dealing with delayed/mistake payments with my current self-directed IRA administrator.

I mean in 08 to 2011  it was painful writing checks to sell real estate..

Look at the usual pain points for owner occupant buyers: old systems, scary repairs, septics, lead paint blah blah....if you are comfortable fixing one or more of those you are already ahead.

I also like to do the mechanicals that I know are going to be a pain in the next 5 years.  

There's a win win here as I have some capital to invest again (those 25% downpayments are a pain!)