I was given the advice of having the compression checked in reference to my hard starting problem. My results as follows:
Cyl 1: 240psi
Cyl 2: 255psi
Cyl 3: 360psi
Cyl 4: 360psi
Cyl 5: 360psi

After that bad news I had them do a leakdown on those two cylinders which revealed it was mainly leaking at the rings. (some from intake/exhaust valves)

So what are my options besides only driving when it's warm out?

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'84 190d 2.2 - Silver
Converted to 5-Speed
'84 190d 2.2 - Blue
Factory 5-Speed

'76 300D (W115)
Sold, found again in less auspicious circumstances