I bet they wait until January or February so they don’t have to pay the tax on those gains for another year (which is why we may be seeing less selling this month than in a normal cycle).

I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

To pay for this, I used a heloc on my current home.

Focus on paying them off (smallest to largest), and you'll be living large in 20 years.

If I sell one house per year, it will pay for itself.

So, you can do a land contract for 12 months, which should allow lender to credit you full value of the land vs the purchase price, but the loan will pay off the land contract, so the lender maintains first lien position.Can't help you with the rest of your question, but you should be able to search for "CPA" here on BP to find experts to reach out to.

Hey @Keagan Scott, so I don't have any insight into Gary, IN but here is a blurb -"Those looking to rent out their properties for less than 30 days (about 4 and a half weeks) will have to get a permit, pay a one-time $150 fee, and have a city business license.

What should I do if my tenant isn't paying rent?""

Plus, it integrates seamlessly with accounting tools like QuickBooks, making bookkeeping much more straightforward.Whichever account you choose, look for one with no monthly fees, online banking, and features like automatic bill pay.

You can't directly do something to allow you to sell the flip, and buy the triplex without paying gains.