I ran 2 bed and breakfasts for 24 years, living among the guests which is a little different but essentially the same, it’s just running a business while house hacking.

I think it gives it a older stately look.Regarding the wooden columns, if they are not too far gone, I've seen Bondo used to patch them up ( I have no idea how long it holds though).I think just doing a cut back on the foliage would be a big improvement, plus a driveway for off street parking.And straightening the porch roof line might make a more "put together look" for the property.Pretty grass, but it's so long--like waving fields of grain.I wonder how many pancake breakfasts have been served in this home over the last 100 years--all of the different people who have lived there.Anyway, for fun, I make a mockup with the foliage cut back and some other upgrades (which might not pay off in a flip).Good Luck!

I replaced both bathrooms, tiled the floor, built a breakfast bar in the kitchen, painted cabinets and did a concrete overlay for all the countertops.  

They'll want to know if the area has a strong rental market and if there are any potential hazards that may affect the property's value or income potential.Overall ;) - make sure your property is bringing home the bacon, your expenses aren't too high, you're an experienced landlord, your credit score is top-notch, and your property is in a great location.

I kind of ultimate house hacked for about 25 years owning 2 bed and breakfasts and living amongst the guests.

I recommend GRID and Cashflow Breakfast Club.  

Travelers often get in late and have to be at work the next day so these little supplies allow them to either have a snack when they get in or grab a quick breakfast in the morning.

I owned bed and breakfasts for about 24 years and effectively house hacked those living among the guests.

We've always used a motel/hotel with pool and a good breakfast because of cleaning fees and chore lists. 

Trash being taken out prevents it from stinking up the property too much before cleaners arrive (haven’t figured out yet why most people choose to cook bacon for breakfast on the same morning they check out).