If you can negotiate a lower sales price great.

But what’s the best way to...I guess lower the risk of hiring a crappy manager.

Which will lower your capital available for investments.Option 2.

It is much better to just pay a 30yr down faster and maintain the flexibility of a lower payment.

Those are what hooked me originally and I have analyzed hundreds of properties since. a 4 unit would probably require a lower acquisition cost than a 5-6 unit due to residential vs commercial loan requirements, but there are some of both available depending on where exactly you are looking to invest.

I can then find another good deal- used vehicle for below market value, with lower miles, and a bit newer. 

It's extra work/headache for a potential buyer down the road if they ever want to refinance or sell plus it could be a potentially higher interest rate and down payment requirements so this in turn should make the market price lower than typical condo prices but shouldn't be a deal killer as there are plenty of community banks to shop around.

However, when I do a property search on the tax assessors website, many times the Fair Market Value listed by the county is much lower than the properties list price?  

It's an 1700 square foot home with 4 beds and 2 full baths in the lower unit in turn key condition. 

I requested the lender to explain it and stated that they are not sure why it was quoted at the lower rate but the actual amount is the increased rate.