People are generally referring to this type of entry as contra-expense or atleast that's how I interpreted.In the PA tax return, this line item was highlighted in Red and hence the question

The involvement of onsite management, often seen as a potential red flag, can lead to the property failing crucial qualification tests.

HELOCS do exist for rental properties but you are usually capped at 65-70ltv and these will most likely require a full underwrite that takes into consideration taxes, income, dti and all the normal quasi-associated red tape.

The involvement of onsite management, often seen as a potential red flag, can lead to the property failing crucial qualification tests.

The shutters would be for looks only, so no need to have an arched top IMO.Cool, the trim and eaves are a dark red now.

Now, even though the red tape has lessened and selling might be feasible, the current high interest rates could make it difficult to find buyers willing to invest at a price that reflects the property’s true value.

So things that are a red flag for me may be fine for someone more aggressive.

Are you aware of any pitfalls or "red flags" an investor should be aware of that might prevent qualifying for a conventional in this scenario?

We'll typically pay $25-50 each time we have to schedule a group viewing or inspection, delivered as an e-certificate from either Longhorn Steakhouse, Red Lobster, or Amazon.Works like a charm!

It can take 20 years to develop with all the red tape.