Assuming that the act of wholesaling is legal in your area, have all the costs associated with closing go through the title company. 

@Philip Jones we've helped our clients do over a hundred.As some of the lenders posting have pointed out, the challenges are:1) Property value and corresponding loan size2) Appraisals have much better comparables than 5 years ago, but may still be an issue.3) Property condition can be an issue via the appraisal4) Ownership seasoning - most lenders looking for 6+ months or incredible documentation for cost of improvements made.5) Most DSR lenders require professional property management.Always try a small local bank or credit union, but most will expect you to transfer your business bank accounts over to them. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

It is the IRS rules around short term rentals.Loophole - A way of avoiding or escaping a cost or legal burden that would otherwise apply by means of an omission or ambiguity in the wording of a contract or law.

She's probably using one floating around the office, one you provided, or one she bought from an attorney that's full of legal jargon and missing important clauses.

@George Fleming Better make sure it's legal to do that.

Legally you can claim estoppel and latches as a defense as they let it go on for so many years and you relied on it when buying. 

A good vendor will often provide insights and a documented professional opinion, which can serve as third-party confirmation.

Property Condition Report: Document the property's condition with the tenant to manage future damage claims.4.

Short term, assuming the real estate lobby doesn't sue this to keep delaying/appealing, once it goes into effect there will be no more broker fees paid by tenant *unless they hire the broker*Some long term effects I can predict already: - Landlords now having to absorb broker fees will bake this into the rent (e.g. how "no fee" units typically are priced a little higher than other units) - Real estate board will require another document (or checkbox) for tenants to sign stating that they're hiring the listing broker and responsible for compensating them for their fee *if* they apply and are approved- Regular New Yorkers will have an even harder time to find an apartment because you cannot legislate/regulate away a housing crises...