If I am being greedy, you can tell me, but be gentle, I only own two properties lol

Other factors to consider are what you plans are for the future (value add rehab, restructuring, selling the property soon, etc) and whether or not there are any events on your personal horizon that may impact your ability to refi later. 

It adds a personal touch and helps guests feel more at home.Things to Be Aware OfLocal Regulations: Check local short-term rental regulations, including permits, taxes, and any zoning laws that may affect your ability to rent the property.Cleaning and Maintenance: Short-term rentals require frequent cleaning and upkeep.

House hacking was owning with roommates.  

Look online or go in person and get all their eviction paperwork.3. 

Hey Arron,I have not personally heard of them but would recommend looking into their online presence/reviews.

I only have student loan debtI have a full-time remote jobI have no prior experience in real estate investingMy credit score is high 700'sHere are the details about the property in Zenda,WI:Asking price: $235KIt’s being sold by out-of-state heirsIt needs at least $50K in repairs and updatesThe neighboring house recently sold for $235K (though I don’t have details on its condition before the sale)A family friend who owns a construction company assessed the property and noted the following:Replacement Needed: Furnace, Water Heater, Water Softener, Floor (concrete replacement needed due to unevenness), Roof, GuttersUpdates Needed: 1.5 BathroomsConcerns: Black mold and water leak marks upstairsRemodel Suggestion: The staircase is very steep and narrow; recommended to relocate and extend it into the living spaceAdditional Work: The property slopes downward, allowing rain to flow into the house.

But from what you described this has gotten PERSONAL.  

Lenders will not consider your personal DTI to qualify.

As for the information out there that's offered, I listen, form my thoughts on what I heard by doing some due diligence, but more importantly, I take what I heard and formulate my own approach or outlook on the subject.