I keep telling myself I'm having anxiety over something that hasn't happened and likely won't happen.  

In some cases, gross income can include recurring capital gains or unrealized income, winnings from a day of gambling, rental income, and sometimes even interest earned on retirement accounts.

PocketGuardWhat makes it unique: PocketGuard is a comprehensive finance app that allows you to monitor your net worth, watch your cash flow, and track all of your recurring expenses.

Alternatively, you can consider investing your cash in passive investment opportunities with recurring cash flow.Should You Sell Your Investment Property?

(B) That everyone currently doing STR in the market loves it, enjoys what there doing, is having a great time, has the free time to do it, is loving life and not stressed out, time crunched, anxiety ridden and generally stress wracked. 

Enter recurring charges and automatic late fees.

In most situations the tenant is 100% responsible for the initial security deposit payment, and any recurring utility charges. 

If you want to do the month-to-month landlord duties to save on recurring management fees, there are companies / agents out there who will list the property, screen the tenants, and place a solid tenant, usually for about 1 month's rent. 

Sure it can be a write off, but my question is if it is the highest and best use of your time (or the given employees time) to be running a skid steer - transporting it, storage, maintenance, cleaning, etc, and if it still makes sense if you need to hire someone to run it for you and take care of the other things.Add up all those recurring costs - maintaining the machine, maintaining the trailer, having a large enough truck to tow it, insurance and registration for all of the above, your time or your employees time related to all of the above...even at $14k a year it might be attractive enough to keep paying that and having them drop it off at the job site for you.A brand new machine could easily cost you over 6 figures - that's 7 years of rentals at $14k/year before including all the holding costs. 

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.