I think that could give me a big chance that the rent could cover 1.3k and maybe with a small lunch money as an extra.

What is this extra fee for? 

National dues could see a raise in the multiples, or come with a special assessment of an extra $500.

They also provide year-end statements and are required to provide a 1099 for tax purposes, but many charge extra for these.Having an actual receipt won't help you with your taxes, but as you have learned, can help you track expenses.

Bottom line… I’d be willing to come in a few thousand dollars more on my offer if it means there’s future potential to earn that much extra in rent each month, and I’m not sure what to do.

Start with a primary home, maybe a 4 bedroom house and house hack. 0 DOWN VA loan ... all you need is closing costs with is usually around 3% of three closing costs.

They usually have regulations on the # of dwellings per acre and I’d hate for you to spend money designing bringing utilities to the site only to be in a city council meeting where the local neighbors shut down the proposed development. 

From my understanding, if its passive income, just a room-by-room rental, it would go on your schedule E just like any other rental. if its active, like a short term rental situation or mid-term, something like an airbnb or bed and breakfast where you're actively including extras, it would be filed on a schedule C. disclaimer, im not a tax person, so double check this with your tax pro. when you go to qualify for your next purchase, whether that's for primary or inv., using a full-doc loan... if its schedule C, you would need to do a 2 year average of this income in order to use it. its looked at as a business, and self employment income. if its schedule E, theoretically you could use the schedule E income calculations just like any other rental even after the first filing.

If you're difficult to deal with or require extra handling (i.e. pays each month's rent in 2 or 3 payments) there's a $250 upcharge on what the rent increase would be normally.

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.