Here is some info: SF STR FAQAssuming the info is up-to-date, it must be your permanent residence (you must live at the property for a minimum 275 days a year), you can rent unhosted a max of 90 nights a year, you need a business license, and you need to pay the city $925 for a STR certificate.

After spending 25 years as a Software Engineering and Product leader, I’m now exploring the world of real estate investing (REI) and looking forward to learning from all of you.My goal is to leverage my current investments and savings to build a real estate portfolio that will eventually allow me to transition away from my current career.

I want to get some info on those properties maybe a good BRRR.  

Eliminate debt, establish a budget, and save.

Makani, there has been some good info shared by other Hawaii realtors.

Was looking to save where possible in this market but the method I proposed is not worth the consequences. looks like 20% down it is!

My goal is 25 doors in 5 years, my struggle right now is deciding to either go back to work and save up money to continue or come up with a way to leverage financing to stay afloat myself and stick with it, waking up everyday 100% dedicated to my real estate. 

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

If you paid under $230k, you’d save $30k in federal capital gains taxes and maybe another $15k or more in state income taxes.

My suggestions would be in this order:(a) Determine the type of financing you qualify for - this will short cut the process considerably and save time on investment angles and next steps.