The agreement says they will return it to you in the same condition it was received so that should be your expectation.As for the dishwasher, you should charge him if the damage would have been discovered by an ordinary tenant.

Would this be through ordinary mortgage brokers?

The IRS has "Ordinary and Necessary" as a guide for what is deductible. 

It's not as ordinary as it is for someone to rent a "lower-end-of-the-bellcurve" home, but I know several high earners who have been renting for the past 5-10 years for a slurry of different reasons.  

Assuming nothing out of the ordinary, it will all come down to the taxes.

If the activities rise to the level of a trade or business and you/the entity are/is a dealer with respect to the mentioned properties, the income would not be capital gains but instead ordinary trade or business income subject to SE taxes.I'd recommend you engage a professional to help make the decision (especially if you expect first year net to be $300k), as there are qualitative and quantitative factors that need to be considered. 

@Brit F.Great advice!

Otherwise, I love seeing out-of-the-ordinary rentals available as I feel that with the snowflake movement, a lot of younger renters are looking to move away from the beige and grey of everything else and not enough owners are taking the risk you're taking to grab them!

@Brit F.

If you just deposited her ordinary check clearing can take 10 days.