@Cameron Marmon I cannot really say definitively whether you should hold or sell but I can give you some points to consider.
The first rental is the toughest because if you have a vacancy then 100% of your portfolio is vacant. If you have a bad tenant then 100% of your tenants are bad. It seems to level out at about 4. So I understand your angst. But you have to just stick it out.
Given a roughly 5% cap rate for a class A/B property in DFW you should net $1,350 after fixed non mortgage costs like taxes, insurance, HOA. Based on my own $300K+ rentals I think $2,000 to $2,200 is very doable.
I know some people consider appreciation just the icing on the cake but you need to also consider appreciation as a part of your overall return on investment. Some times in the market you get wads of cash flow and no appreciation and other times it is the opposite, like now. You need to combine the two. Think of it like stocks. Some pay dividends and some growth.
If you have a well paying career job and you are relatively far away from retirement then you don't need to worry about cash flow today. I know a lot of investors consider cash flow the holy grail and won't consider holding a property that doesn't cash flow but you don't need the cash flow today, you need it in the future. Concentrate on good properties in great neighborhoods. Particularly newer homes. That way, a couple of decades from now when you retire you will have fine properties that have not only appreciated a lot more because of the neighborhood demand but more importantly cash flow handsomely and that are only 20 years old (as apposed to 50 and costing you a lot of maintenance that you cannot afford). For more on this school of thought you should check out @Erion Shehaj Investing Architect blog.
I wouldn't worry so much about tenants trashing your fine house. Those class of tenants usually take good care of the property. But I would worry about how it will make you feel. Renting out your old home is kind of like having your ex girlfriend around along with the new guy she is sleeping with.
You should definitely consider taking advantage of the tax break on selling your old home. I'm not 100% sure but I believe you can still be taxed on this sale indirectly by the AMT.
Managing higher end rentals yourself is easier than lower end. I would not take the equity out and buy three $125K properties. The cash flow numbers for these class C/D properties always look great on paper but they never pan out. They won't appreciate as fast. They will incur more wear and tear. They will have more vacancies.
I look forward to hearing about your final decision and the reasoning behind it.