I thought the regular "free" Stessa account was ok.

In addition to what was said above, for the software that has a free trial option, sign up for it and use the software for a day (or at least a few hours) as if you are using it for real, then call their customer support too and get a feel for that. 

created a free eFiling option for 1099s directly with the IRS.

Feel free to inquire about their staff qualifications if it's a larger organization.2.

These platforms typically have billing policies where you pay a per unit fee per month to the software and you get regular updates and support each month.There are a number of low-cost platforms available that are able to offer you a lower price by passing along some of the costs to your tenants (payment processing fees, applications, tenant screening, etc).

Factor in carrying costs (utilities, taxes, insurance).2.

Feel free to message me if you want to chat about it

If it's a roth IRA, you may be able to take out the principle tax/penalty free.

Would it generally be a location that tends to have a higher cost of living? 

Free healthcare free cell phones free housing.