It is an older home and I know there will be some larger ticket repairs needed in the coming year(s) (roof specifically will likely need work soon).

The home must be in the owner's sole control year-round. 

As @Jefferson Black pointed out, furnishing a rental is a hefty ticket and the turnover can be a lot to manage (esp. if you happen to be out of state/country).

I do see alot of people searching for STR'S with private pools.I also see people buying multiple pool cabins, so they absolutely seem to be paying off.Many of these are indoor heated pools that can be used year round.

Most markets in Florida are quite lucrative and have higher and consistent occupancy rates year-round because of the weather.

Stunning nature with the Pacific ocean and gigantic Santa Monica Mountain Range out the door with year round near perfect weather.Close to everything from Malibu to Calabassas, Ojai, Santa Barbara etc and within the same 45 min to 1 hour distance ( traffic depending) to 3 commercial airports, namely LAX, BUR, SBA.The university, USCCI is the only one of its kind growing in leaps and bounds while general enrollment numbers are in decline everywhere else along the CA coast.

I do owner occupy this property and so I was able to get in during the first round of bids.

We add the 12 year's borrowed money return with compounding total will be $129235,  Add  $161355 cash value, the total will be $290590.You know for $100k , 10% rate compounding 12 years will get $313843, higher that your $290590.Conclusion: in the above example,  WL will never catch the other investment because WL only compounding at 9.6%, below the 10% of the other investment.BTW, you know 9.6% compounding 12 years is  $300418,  because the $290590 may have rounding error when I do the rough calculation. 

They move to the HOA to get away from the downtown scene.

Our contractor said we should definitely replace the electric panel, but might be able to get away with using the old wiring.