That will require a rough and final inspection. 2) When installing drywall you will need a nail/screw pattern inspection. 3) You will need to provide 'conditioned air' to these rooms..how are you going to do this and that will require inspection.Will you have to increase the size of the electrical panel?

This can lead to consistent limit increases every quarter, which opens up even more opportunities for growth.Having good rapport or a strong relationship with a credible accountant to help simplify and oversee this process is an amazing idea and highly recommended.

If the rate is reasonable then it may make sense to try to save fast to get to the 3.5% down payment on a double or triple - househacking may allow you to increase your savings rate and pay down that loan even faster.As for estimating costs, closing in NY factor at least 1% of the mortgage amount for tax, plus $1500-2000 for lawyer, title and fees, then the amount required by the bank for escrow will depend on the actual property taxes and insurance.

Also considering live and flip, or make our first home we buy an opportunity to increase our income as well (renting basement or part of the unit).

Live in one unit and rent out the others to cover your mortgage.Seller Financing: Negotiate terms with the property seller where they act as the lender, often requiring a smaller down payment and bypassing traditional underwriting.Partnerships or Joint Ventures: Partner with an investor who provides the capital in exchange for a share of the property’s equity or income.Lease Options: Use a rent-to-own agreement, which allows you to control the property while saving for a formal purchase.BRRRR Method (Buy, Rehab, Rent, Refinance, Repeat): Acquire a distressed property with short-term financing, rehab it to increase value, rent it out, and refinance to recoup your initial investment.Pro TipStay in close communication with your lender as you approach your next purchase.

Listing it “as is” with a $25k rehab concession can attract these buyers.Consider these options:List on investor-focused platforms like Roofstock or BiggerPockets or Facebook Marketplaces, where you’ll find buyers who appreciate tenant-occupied properties.Network with local investors or REI groups in your area to find someone looking for a turnkey rental with upside potential.Hire a real estate agent experienced in selling tenant-occupied properties, but adjust your pricing to cover commissions if needed.Make sure to highlight the stable tenants and ADU potential—those could be big selling points!

You can show a packet to the mayor of the city, and they'll focus on a 3d picture of the development rather than 10 bullet points on how it will increase affordable housing supply. 

It’s easy to find tenants, population/jobs are increasing, and property taxes/insurance aren’t skyrocketing. 

When we tell them our opening bid is $1.5M they try and negotiate off the $500k because that was the original loan balance but due to other circumstances like modifications etc. the loan balance has increased significantly. 

@Ben Cochran I hope you have factored STR tax savings into your cashflow and ROI as it can be significant.Leveraging equity to purchase a short-term rental (STR) in Tampa Bay can diversify your portfolio and potentially generate strong cash flow, but it also increases your financial risk.While your properties hold significant equity, adding debt from HELOCs or a DSCR loan could strain your finances if STR performance fluctuates or costs rise.