Our current renter is likely to be renting for 4 years as she has kids at local school and 4 years would see them through to going to college.We have an old detached 1.5 garage that has functional automatic garage door, and just fits their car....not that they do it very often as I think it is a challenge. 

But it automatically kicks you out if you don't respond to the CSR's latest message, even if that message is a statement and not a question. 

If all is going normally (including typical BS delays – we are not naïve), our documents grant an automatic 6-month extension.Since 2010, we’ve had exactly one issue with this.

@Patrick Irish based on what you say, the Sec 121 Exclusion and the 1031 Exchange both seem like they'd be good options for you to defer capital gains on sale of the townhouse.Sec 121 Exclusion has 3 requirements: First, Determine whether any of the automatic disqualifications apply (acquired property through 1031 exchange in last 5 years, or subject to Expat taxes)Next, meet the ownership requirement -> you owned the home for at least 24 months (2 years) out of the last 5 years leading up to the date of sale (date of the closing)Finally, meet the residence requirement -> owned the home and used it as your residence for at least 24 months (or 730 days) of the previous 5 yearsThere is no “Wiggle Room” but there is a Sec 121 “partial exclusion” for people like you that missed the residence requirement by a few months.

Although mine does populate a trial balance and balance sheet automatically also.

Both the new and old accountant send monthly statements, but the old accountant also used to automatically send me an annual statement at the end of the year for my taxes which is really helpful. 

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.

One problem I'm running into is that I have to use Stripe for my payment collection for VRBO bookings so it does not automatically collect and remit taxes...trying to set it up to do this through Stripe but it's not as straightforward as one would think 

Enter recurring charges and automatic late fees.