We plan to hold our primary residence and rent it out.

My current goal is to start with house hacking and move on to long-term single-family rentals.

In the last 6 months i've acquired two more short term rentals in the Poipu Beach area and completed a 1031 exchange.

Investment Info:Small multi-family (2-4 units) buy & hold investment.

I'm so confused... do y'all do other insurance on top of homeowners policies on your short term and medium term rentals?  

The HOA is money hungry so they will never ban short term rentals. 

o Bridge (rehab) or long term (30-year fixed)?

Prepayment penalties- usually 1-5 year terms.

The condo I am looking at is close to the new Aquarium that is going up, the new Grand Village, etc..I feel like as a buy and hold it is fantastic since it is guaranteed to appreciate but also as a completely remodeled 3/3 so close to the strip, I could do well with STR and at a longer renting period as opposed to golf/lake rentals.

Getting into the story behind this one..This deal was sourced from a large corporate wholesaler (no names) Originally listed as 179,999 as a "wholetail" deal with an "ARV" of 250,000 I walked the house and estimated it needed little in terms of repairs, though I knew a realistic ARV was between 215-230 However, there were tenants in the house without a lease agreement with the current landlord.