Fortunately, his wife was a friend of my wife from college and I got the advice for free.

It might not be the best idea to embark on both at once, but fortune favors the bold, no risk no reward, etc. 

I am fortunate to be in a position with my current house hack where I am able to put on my tenant hat and think about what improvements would make my two units appeal to a larger tenant pool at a higher rent rate when the time comes to move out.A project i have been thinking about is adding central AC and splitting out the heat/ gas bill. 

I am sorry you have had bad experiences and hope my fortunes don’t change to mirror yours. 

San Diego City Council passes first reading of short-term vacation rental ordinance (msn.com)I feel fortunate that our STRs are in Mission Beach (30% quota), have used professional PM for many years (ideally responsive to complaints and have paid all fees/taxes, we should qualify as a good actor), and it is two units (either one for wife and one for me, or one for wife and I and one for son, or ...).If you find the actual text of the new regulation, please IM me the source.

It wasn’t fun but fortunately for me it wasn’t leaking.

Fortunately, I am almost certified (test next month) and I am combing the MLS pretty often in addition to the letters/off-market efforts. 

I see a lot of crazy high end Joshua Tree Air Bnb's and figure it must cost a fortune to get materials and workers out there.

It was quite the process but fortunately I was able to engineer, design & install the entire system. 

Fortunately, I don’t need 2 dryers, so this won’t work for me.