I would raise the rent gradually (whole boiling frog analogy).

So yes, replacing an entire roof does count against your annual gross income, but it would do so gradually.

You would need to do a little modelling to find out the exact percentages, but if all your mortgages a newish (<5yrs), then my conjecture (at this point, unless I break out the HP) is you should start pay down on the newest ones first, then gradually shift your payments towards progressively older mortgages.

I plan on wholesaling first then gradually moving to buy and hold.

Policies tend to change slowly and gradually.

This assures that they'll gradually get their money back AND make solid returns at the same time.

If you want to keep this plex property long term after you move then I'd suggest keeping the cash flow and let your tenants' rents grow the equity gradually over time instead of dumping extra cash into the house to grow your equity faster.

We started off in really rough stuff & have gradually focused our attention on higher end properties as the war chest grew.

If a property with those parameters should produce 6-8% returns with gradual increases as the market rises.

In contrast, if you gradually make principal payments on your $1 million of pre-TCJA home acquisition debt, you won’t be able to treat any portion of an additional home loan taken in 2018–2025 as home acquisition debt because your existing loan will absorb the entire $750,000 TCJA limit."