I have gone down that road and it is a pain in the rear.

Pain In The A$$

It's not just rookies who are feeling the pains of a tougher market.

Less pain, more fun. 

I would also interview tenants and see if any seem to be pains in the butt.

Pain, time, effort and indigestion of obtaining loans isn't discussed enough on here.   

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.

The BP guys are amazing, likeable, and sharp as a tack, and I love to hear everyone's journey to success. 

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