All depends on the market or if you want to be one of the only properties to offer a hot tub in your market, which could potentially tip your property to a top line in revenue and occupancy. 

@Jonathan Klemm Plans are to either house hack again, potentially live-in flip or maybe venture into 5+ unit commercial

The cash flow from the properties I am looking @ are low..The buildings are all under performing on what they could potentially get for rent..I see a lot of room for growth and cash flow on these properties, especially with two major projects in the village getting ready to be completed -more jobs and more foot traffic to Main Street are on the way..Carbon copy of Hudson and early 2000’s... Advice, buying a building that wouldn’t maximize for 15 to 24 months ??

Make sure to research lenders, get pre-approved, and calculate your potential ROI before bidding. 

If you buy a whole portfolio and your projections are off then you are potentially in trouble. 3.

Covering the mortgage isn’t an issue, but I’m considering factors like: Multi-Family: House hacking would help offset costs right away, but I’d likely need to put money into renovations upfront.Single-Family: Easier move-in with no immediate renovations needed, plus potentially lower tenant turnover once I rent it out For those who have been in a similar situation, what did you choose and why?

Digging down is a project I am just finishing up.... it is exhausting but potentially worth it.

Yes @Akash Sky that is considered ordinary income

You should also verify whether the lease agreement allows for ownership transfer without landowner approval.Owning the trailer means assuming responsibility for lot rent, potential removal costs, and liability risks.

The BRRRR method (Buy, Rehab, Rent, Refinance, Repeat) could also be a great strategy to recycle your capital.To find deals, try direct mail campaigns targeting absentee owners or distressed properties, or go driving for dollars in neighborhoods with strong rental potential.