We managed to navigate it, but it was a lesson in the importance of understanding both federal and state regulations.Given your location in Boston, Massachusetts, it's especially pertinent to consult with a qualified intermediary or tax professional familiar with both federal and Massachusetts state laws to ensure a smooth exchange process.

If you qualify, you can use passive losses, like those from depreciation, to offset your active income.

No W2 is required for DSCR Loans - one of the main benefits as its strictly no income verification for qualifying.

The structure for this is a discounted sale, lease back, buy back.One of the partners is a qualified intermediary as well that understands the plumbing behind it to make it 1031 compliant.If you have any questions on that - feel free to give me a buzz.

Do we need to go through the whole condemnation process to qualify the transaction for a 1033 exchange?

I’m not skilled in repairs and live in a high-cost, tenant-friendly area, what would be the best way to invest my money?

Some states (NOT ALL) offer reciprocity for real estate licenses in certain other states, BUT that just means that if you have a license in one state that you can use that to qualify for a license in other states that offer that reciprocity.

For instance, FHA guidelines are very strict and restrictive when it comes to using departing-residence rental income to qualify for a new FHA loan (such as the 100-mile rule).

What makes it slow in this case is that you don't really start seeing real cash flow until after year five but it's more effective than rentals in that there is little to no maintenance.Sure you can live in a home while fixing it up with the intention of selling it for a nice profit later but I think many people are already doing that and the buyers of slow flips now also have that opportunity without having to qualify with a bank.

Aging reports would be another avenue to explore, but again, may not even have these.Lastly, while maybe this property is in a desirable area of town with strong demand from highly qualified tenants, but I get the impression this is a rough part of town, with very limited demand from tenants.