I know the state has CA fair plan insurance for high risk properties and I know its cost.  

Hello, I am planning on purchase two triplexes that have a single water meter for each property.

I plan to manage this property myself, manage the finances, manage the tenet forms and etc all by myself so I can learn how to do everything right away when I'm first starting.

I’m starting with just 1 listing but plan to recruit neighbors in my beach market to list on my custom website tailored to our community / market so I hope to be at 10+ listings soon even though I only own & operate 1 right now.Guesty’s pricing did not appear to be competitive and for someone starting with fewer than 4 units but planning to scale up behind that, Guesty does not offer a migration path from their “for hosts” product to their “for pros” version - it would have been a complete redo on setting everything up.

Looking for some opinions please..I am on track to close on my second investment property (3/2)  in a few weeks or so with flexible plans for the Seller to rent it back at a discount for a couple months. 

It 100% is possible to limits but you need to plan around the Excess Biz Loss rules from TCJA.

.), I personally don't like properties with HOAs if your plan is to run them as STRs.  

To determine if the expense should be classified as a capital improvement or a deductible repair, the context of the expense is very important.An example is, if an item of expenditure is part of a general plan of modernization, renovation or rehabilitation to equipment or other business property, it typically must be capitalized even though on its own it would be currently deductible.According to IRS Code, expenses that you must capitalize are those that:Materially increase valueSubstantially prolong useful life (including replacement of deteriorating assets)Adapt the property to a new or different useHowever, you are allowed to deduct expenses and fees for routine maintenance and repairs that help keep the property in efficient operating condition.

Hi @Douglas Alexander, I've used the VA loan many times, but never for MFR.You can't use it for more than a 4-unit building, so 1-4 is OK, 5 or more... nope.Great plan though to house-hack it.Let me know how your research turns out ref. building from scratch.Could be an interesting idea... build like a 3/2 for your family and 3 more smaller units.Then when you move out, you can rent the 3/2 for more obviously and could earn some good cash flow.

I plan to keep going through and watching their content and getting what I can.