Our goal is to eventually use it as an our home for retirement and also for a getaway in Summers and Winters. 

Once the property is rehabbed, an investor if they have taken a hard money loan will take out a conventional loan or a DSCR loan to pay off the hard money loan (HML) to convert the HML loan to a long term loan.

Unless rents increase faster than inflation, no matter how many properties you own, you will eventually be forced back to work because you will not be able to pay future inflated prices.No rent control of any kind.

The app automatically uploads the receipt image to a project-specific receipts folder, which we can then convert to a transaction.3.

However, if you converted the property to your primary residence and qualified for the exclusion when you sold the property, you wouldn't get the full exclusion; you would get a proration between the number of years it was held as a rental and as your primary residence.

Our leases auto-convert to a MTM after 1 year and I prefer that; if I have to evict (rare) I terminate the tenancy at the same time, which is easy on an MTM and avoids a prolonged process.Most of our tenants have been with us for several years.

.)- Review previous rent ledger for patterns to be aware of, note their lease in PMC software- Try to convert to our Lease, to make it easier on our staff (we don't tell tenants they don't have to do this)- Opportunity to renew/extend lease with increase?

We spent about a year studying before we made our first jump into buying our first property but eventually you just have to do it.

The home is now being converted to a rental. 

@Bryan SimmonsHey Bryan,Great plan and yes that is a house hack, tax wise it is a mixed use property so one part is personal and one part is a rentalIf you are remote pick the market and run the numbers, but remember the tax benefits only apply to the rental portion so you want strong income and clean trackingStarting with a 2 to 4 unit is great because you can use low down payment financing, and once you rent units out you can deduct legit rental expenses like repairs, insurance, utilities allocated to the rental side, and rental portion mortgage interestBig tax win is depreciation on the rental portion, just make sure you separate personal vs rental expenses because only the rental share is deductibleIf you move out later and convert it to a full rental your deductions expand, but depreciation lowers basis and can trigger recapture when you sell unless you 1031Also watch passive loss limits since high W2 income can restrict how much loss you can use each year