Keep pushing forward, and soon, you'll see the rewards of your hard work and determination.

When you get one right the reward is huge.

I manage on Oahu in Hawaii and I would assume based on things that I have heard from other hosts and managers in CA that the conversation around regulation would be somewhat similar given that it is a highly desirable destination for both guests and investors in the STR space.Speaking only to what I have experience with here - there seem to be three types of zones that vacation rentals fall into - on one hand you have zones where they are illegal, and while it is possible to run and gun in these areas I don't think the risk is worth the reward if you get caught.

Mine rewards agents three ways:1.

I like this idea because it rewards the tenant by allowing flexibility with their rent payments and rewards me with a bit of extra cashflow. 

It's like combining old-school charm with some modern tweaks.

People think he has a rough around the edges charm and you should just suck it up and laugh.

Another thing I'd highly recommend is talking to property managers on BP to get some feedback-- it's probably very rewarding and can produce income without many starting costs, but it does come with headaches.By thinking about your next steps, you're already on the right track.

It's all risk vs reward..... and if you feels there's enough reward, risk it."

It's true you get a tax deduction for your mortgage, but you also pay taxes on whatever else you decide to do with that money.I would list all of your known investment opportunities, what you think the after tax returns would be, and a risk level 1-5.If paying the mortgage is a clear standout on that list on a risk/reward basis, I would spread out the $60k over a period of time and apply it to principal.You might have other goals like cashflow or reducing risk which might weight towards paydown also.