Here's a list of things to track:- Formal lease application- Formal signed and executed lease specific to your state- Payment history (I recommend using online rent collection like Apartments.com, RentRedi, etc)- Maintenance requests and receipts- Accounting for all rental-related expenses (repairs, utilities, etc) The more you treat it like a business, the more helpful you are to your CPA come tax time. 

The behavior is a bit off, but not surprising for a mom & pop landlord.We tell our residents exactly what we need from them for the application. 

We use efroms.com for our rental application.

I tried to track finances on both Stessa and Hemlane.

But, with a strong application process, we don’t have many evictions.  

.- To utilize the Mills Act requires a few things: An application (not free), inspections, and most importantly a contract with the city in which you promise to rehab and maintain the historic nature of the property.- The inspections are only 5 years, but tenants are not likely to take care of them home as well as you, and refurbishing hardwood, lath and plaster, and anything else is going to be much more expensive than the typical Landlord special (white paint, and grey LVP)It will all come down to making your numbers work.

Capital gains are calculated as:Sale Price - (Original Purchase Price + Capital Improvements + Selling Costs) - depreciation (if applicable) = Capital GainYour mortgage or HELOC balance does not affect this calculation—it only determines how much cash you take home after the sale.In Massachusetts, if the home was your primary residence for at least 2 out of the last 5 years, you may qualify for the Section 121 Exclusion, allowing you to exclude up to $250,000 (single) or $500,000 (married filing jointly) of the gain from federal capital gains tax.

I'm looking to finance the project long term in a way that is helps me create positive cashflow.

Thirdly, financing and potentially selling later on could be challenging again with the part of the plan being on a campground. 

I'm not sure if this forum is still active, but I'm looking to chat with a few real estate investors in Ontario who may be interested in raising funds by selling fractional shares of their property.My co-founder and I...