I do a lot of seller financing and personally keep track of it all myself but it can be a huge pain. 

OBX is a great place, but it will take a very long time to be cash positive based on its current pricing, management fees and the short season.We were going to also use it during offseason but its just a pain to get too.

One of our properties is in Marlborough and it has been a pain.

Problem is most counties property records are so outdated, it would be a major pain in the butt to collect.

So having a proper scalable strategy, getting your numbers correct, and ability to stick to it in spite of short term pain is what makes you wealthy over 10-15 years.

Especially cause I feel your pain.

Leasing, property management, tenant billing, lease administration, finance, capex budgeting, etc.  

Hi Everyone, I'm at the point that my remodel is ready to pain the interior.

The paining done by the tenant was atrocious, cabinets had paint on the sides, baseboards, door & window trim were smeared in paint by these complete idiots.

@Erick AcostaS-Corp can potentially save you on payroll taxes.There are costs associated with the set up of an S-Corp(election costs, payroll tax return costs, income tax return costs, etc).It only makes sense when the savings of the payroll taxes will be more than the administrative costs.You should definitely consult with your tax advisor on if it is right for you.