The hard part is finding a 2–4-unit property that will allow you to live in one unit while having the others cover most or all of your mortgage payment.

Bergford, 12 F.3d at 169.This should be satisfied: (Main Points)The co-ownership may not file a partnership or corporate tax return, conduct business under a common name, execute an agreement identifying any or all of the co-owners as partners, shareholders, or members of a business entity, or otherwise hold itself out as a partnership or other form of business entity (nor may the co-owners hold themselves out as partners, shareholders, or members of a business entity).

There are a number of programs offered by lenders which may be able to help with part or all of your ask.

A portion of or the entire dwelling unit can be used for lodging, including part or all of an accessory structure.Short-Term Rentals are permitted as a Limited Use in the following zoning districts: R-1, R-2, R-4, R-6, R-10, RX, OX, NX, CX, and DX.

Once half (or all) of the rehab is completed, you can then "draw" the money out of the escrow account relative to the cost of the work that has been completed.

There is also a potential 3.8% Net Investment Income TaxState Taxes - Dependent on stateSale of Real estate that is considered InventoryFederal Taxes - up to 37%State Taxes - Dependent on stateSelf-Employment taxes - up to 15.3%If it was a personal residence prior to sale, some or all of the tax from gain may be excluded.

Any provision, whether oral or written, of any lease or other agreement, whereby any provision of this section is waived by a tenant, is contrary to public policy and void.

He had an oral month-to-month lease agreement with the old owner and I continued with that.

Monitor / Review your success  (keep the process active at all times)   From an insurance perspective, the broadest policy form is called a "special form" policy (aka open perils or all-risk). 

Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion