Keep in touch with your lending partners for each one so you can understand whether you need departure residence income to qualify for the next or not.Finally, if you're investing with a Significant other, I recommend considering a "leapfrog" strategy where you buy one, then your partner buys the next, and so on.  

Here are a few strategies to consider for funding a down payment:Partnering: Like Gregory mentioned, finding a partner who can contribute to the down payment in exchange for equity or a profit share is a solid option.HELOC or Cash-Out Refi: If you have equity in your home or another property, a home equity line of credit (HELOC) or cash-out refinance can provide the funds you need.Private Money: Reach out to friends, family, or private investors who may be interested in lending you the down payment with a promissory note.Seller Second: In some cases, the seller might agree to finance a portion of the down payment as a second mortgage.Live Frugally and Save: It takes time, but reducing expenses and setting aside funds from your income is a tried-and-true method.The right approach depends on your situation and deal structure, but a mix of creativity and resourcefulness can go a long way.

Are there better markets or hybrid approaches I should consider (e.g., smaller multifamily properties that accept Section 8 tenants)?

Be mindful of short-term capital gains tax, as profits from flips held for less than a year are taxed as ordinary income, and frequent flipping may result in self-employment taxes.While profits from flips do not qualify for 1031 exchanges (since flips are considered inventory, not investment properties), you can minimize your tax burden by deducting allowable expenses like renovation costs, loan interest, and holding expenses.If you're considering diversifying into rentals, explore opportunities to benefit from long-term tax advantages such as depreciation and lower long-term capital gains rates.

We're exploring creative ways to provide him with the cash needed for the down payment while avoiding triggering a taxable event.One strategy we're considering is purchasing his future primary residence ourselves, making the mortgage payments, and then, once we've built enough equity—comparable to the appraised value of his rental properties—transferring the title to him as a form of exchange.What are your thoughts on this approach?

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Depending on how much time you have to commit to real estate (or want to considering your dollar per hour is probably better spent in dentistry) you may want to consider becoming in LP in a real estate syndication deal.

The tax expert knows more about whether or not the future is affected by changing the use between 2023 and 2024.If you are worried about paying taxes on rental income, you might consider that you can rent your home out tax-free for (I believe this is correct) 14 days of the calendar year. 

Have you considered starting with a market that has strong rental demand and landlord-friendly laws?

A few months go by and unbeknownst to me the escrow account had now drawn negative which triggers the lender to no longer apply what’s considered a “partial” payment to them, given that I’m now paying less that what’s due given the escrow increase required but not relayed to me even though I expected it at some point.Last month I’m on Zillow looking at the value of my properties.