I make a decent amount of money nearly from my W-2 (over 100k) but still not enough to easily buy another property this year especially if I have to put down 20%.

. $220,000 is definitely a lower purchase price amount and really limits you on what you can buy.

Looking to buy Business around Portland metro below $300k.

Investment Info:Single-family residence buy & hold investment.

If you could buy it, what would you do with it as an investment?   

This does not align with buying most buildings in cash.Once you progress in your investing efforts you may come across more UHNW individuals, family offices and institutions who would take the lower return for limiting risk (all cash deal).

I've considered going Dave Ramsey and buying a house with cash and upping my budget to $100k in a smaller market, but that would blow almost all my savings, and $100k just doesn't get you much anymore.

The real value is on the buy side. 

I'm trying to pinpoint my financial strategy in attaining these projects and HMLs are always suggested to me.My goal this year is to buy my first investment.

I would suggest you do both of what you suggest - meaning get either a new mortgage (more conservative route) or HELOC on the townhome and use those funds to buy your next investment property.