If you need financial help, ask under the "Finance, Tax, and Legal" forum.

@Helena Goyvaerts it will be tough without 2+ years of USA tax returns showing you are profitable.Higher interest rates have negatively affected most lenders and many of them are getting more aggressive with offering more flexible programs. 

Spend the $25,000 on a deal not a consultant.

Your loan will be $1,100 a month, add insurance and property tax.

Don’t want to pay taxes on the capital gain.

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.  

Have you consulted with lenders to discuss your budget and options?

Some thoughts to consider:If you sell now, you are unlikely to pay capital gains taxes as your first 250k (500k if married and filling jointly) aren't reported.Doing your first rental remotely is undesirable without 1.)

I truly think I only need 4 more houses to hit my goal and then shift from buying to paying them off.I am not sure if I am thinking about this the right way and I am sure there are things I am not thinking about but below are my thoughts:Pros - I can purchase the houses I need to hit my goal faster - With getting homes fasters the depreciation, tax benefits, amortization, appreciation, rent increases all start sooner - Home prices on average should be lower now then if I buy in 4-5 years - I can take better advantage of leverageCons - I have more risk until I pay the properties off - Less upfront cashflow - Longer timeframe to acquire the properties to reach my goalIf anyone has any opinions or advice I'd love to hear it.

What is the interest rate on borrowing compared to the rate you are earning, then take into consideration the tax consequences.