You have to adjust your expectations to match current reality, which includes higher mortgage rates, higher prices, more expensive taxes and insurance, more competition, etc.

Be aware of tax implications: rental income is taxed in the property’s state and reported on your California return, with deductions for travel, depreciation, and expenses.

. ==== Projected Income ====**Off Season**-$4,000/Month Rent Period: September - May (7 Months) Projected Income: $28,000**Summer 1**-$8,000/Week Rent Period: June (4 Weeks)Projected Income: $32,000**Summer 2**-$8,500/WeekRent Period: July-September (12 Weeks) Projected Income: $102,000**Optional** (Basement Apartment)-$2,000/Month -Rent Period: Year Round Projected Income: $24,000TOTAL PROJECTED INCOME: $186,000 ==== Operating Cost ====-Mortgage: $84,000 ($7,000/Month) -Utilities: $36,200Gas $6,000 ($500/Month) Electricity $6,000 ($500/Month) Internet $2,400 ($200/Month) Garbage $5,000 (Estimate) Pool $4,000 ($250/Week)Landscaping: $4,000 -Mowing: $2,400 ($150/Week)  -Clean Ups: $1,600 (Spring & Fall)-Weekly Turnovers: $8,800 ($550/Week)==== Legal Cost ====Summer Rental Fee: $20,100 (15% of $134K)Sandwich Rental Tax: $6,855 (15% of $45,700) NET PROFFIT: $38,845.00

Would the federal tax liability be $140k at year 5 for the sale, with long term capital gains (ignoring any Net Investment Income Tax)?

Compare this to your total monthly costs, including mortgage, insurance, taxes, vacancy and maintenance.

Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

It’s stable cashflow and long term appreciation and tons of accelerated bonus depreciation on taxes. like most anything in real estate it’s a long term play. 

A colleague recently closed on a 12-unit property in San Antonio and shared that a 6.8% cap rate, combined with lower property taxes, made it a no-brainer.

Start small and aim for properties that cash flow well, even after accounting for taxes, insurance, and repairs.Most importantly, keep taking action!

It will also allow you to pull some cash out if you have the equity and for tax purposes.You can have two VA loans at the same time but having two means that the second home may not qualify for 100%.