Being a real estate professional allows you to treat the income as non-passive, allowing higher high income tax payers to pay less in taxes.

An annual business tax as a hotel of $50 and collection and remittance of transient occupancy tax of 12% from renters is required of all short-term vacation rental operators.

They remit the taxes.

Tax free appreciation and rents significantly trump the loss of depreciation and custodial fees.

I have done it with some contractors taking Paypal where you can use a credit card on that site with a fee, or QuickBooks is another one too.

Quote from @Mary Jo Carruthers: Fees for buyers side has never been set in stone.

This has driven up the property taxes there. 

For every day after the 30-days, the permit fee is reduced by 10% of the permit fee.  

Quote from @Jonathan Bombaci: This year, our management company, which oversees 700+ units in Massachusetts and New Hampshire, spent over $209,000 on attorney fees, primarily related to evictions.

I agree with the others here that say you need to have some skin in the game, if you are going to live there yourself, get an FHA loan rather than owner financing, you can get a 3.5% down loan, personally I do not love these as they require  PMI which is an additional expense, and you also need  bring additional funds for closing at least for taxes, title, attorney and transfer fees . borrowing from anyone else for the down payment, to include a personal loan from the bank is not a good idea, those again will be higher int. rate.