Every dollar going out should be tracked by you via Quickbooks or similar program and all of your vendors receiving over $600 should be sent 1099's (money out). 

Buying tenant occupied in a 3 family can be totally fine, just go in assuming you are inheriting their leases and the program rules, not getting a clean slate.

Quote from @Mike Kirby: Quote from @Jared Townsend: As of January 30, 2026, the National Flood Insurance Program (NFIP) is once again closed for business.

Hi everyone,I’m reaching out to the community for a referral to a rock-solid landlord attorney with deep experience in the Norfolk Housing Court (Dedham/Stoughton) and the Massachusetts Rental Voucher Program (MRVP).I am a live-in landlord (owner-occupant) of multi-family in Canton, MA.

Are there any tricks to establishing this legal entity, or do we need to just accept that this is how this part of the industry operates, and either get with the program or find something else to do?

The dominant amenity might be a lake, trails, glamping units, or even community-driven programming, but the takeaway is the same: you’re underwriting an operating business, not just dirt.

Hello,A friend and I are exploring real estate investing as a long-term strategy, and we are particularly interested in leveraging the VA loan program.

I’m currently sworn into the Delayed Entry Program and will be shipping out soon.

Same for 2-years of job/income stability.Tenant Default: 10-20% probability of eviction or early lease termination.Section 8: Class C rents usually meet program requirements, proper screening still recommended.Vacancies: 10-20%, depending on market conditions and tenant screening.Cashflow vs Appreciation: Should cashflow immediately, at the lower end of relative rent & value appreciation.Class D Properties:Tenant Pool: Majority of FICO scores under 560, little to no good tradelines, lots of collections & chargeoffs, but should have no convictions/evictions in last 12 months.

I'm not aware of any programs that would allow you to get financing as if you were an owner-occupant.