Look for signs of water damage, like stains or discoloration on walls.Roof problems are also common.

If the meetup is directly related to growing your side business or improving your skills, expenses like registration fees, transportation, and meals may qualify as tax-deductible business expenses.

We did it once about 8 yrs ago (although it was structured more like a lease-purchase).

@Jerad GrahamHouse hacking properties should have features like a quadplex with 3-4 bedrooms, flexible layouts, private entrances, and amenities.

I was going to draft up one contract with each LLC as a separate "Owner" with the authorized representative for all, the actual owner, to sign the one contract for all legal entities, but they didn't like this and want to keep all documents separate.I gave them a VERY competitive price quote based on the total portfolio as 1 account with the total number of units.

I would like to find a good reputable contractor that gets in, and does the job [until complete]. 

It would probably be months before the gears that have to turn within the IRS bureaucracy got to filing something like that - unless those gears have already ‘turned’ and you have been given notice of the intent to levy your property.  

As far as the reporting goes, the rental income and losses will most likely be reported on your Schedule E - speak with a tax professional who has expertise in real estate.

We can check the condo and the entire association for things like litigation, under duress, issues with HOA or reserve accounts.

I would like to hire an assistant as the business is growing.