I've been using the GE  GFW148SSMWW // GFT14ESSMWW models which comes to $1,650+ tax for units and stacking kit. 

The data they pull from the tax records on how much a home last sold for, often not updated, or completely wrong.

When we looked at what his cashflow is currently, and then considered what he would net out of a sale post tax, he decided to keep owning the properties.

The home burns and the incredibly over taxed CA FAIR plan has either gone bankrupt or takes years to pay out.2.

Am I setting myself up for a tax nightmare?

Keep in mind taxes go up as do rents.

Invent a global tax (Carbon Tax) and invent a token of credit against those tax's (carbon credits) and shazam a market where traders can buy, sell trade, option, leverage, hedge against these and the flow of them.

Low barrier to entry, low taxes, landlord friendly, some amazing class A and B suburbs and a strong urban core. 

a lot of people will poo poo this, but I also live in a market where cash flow is low, property taxes are high and properties are expensive (which is a relative term).

Hard to give good advice without more info, but since You are single no kids it's hard to beat buying a single family fixer upper and living in it for two years and then selling for tax free profits....I'm a big fan of Waltham these days $.02