There is no rule which says you can't tinker and see what works best for you.I would reconsider about buying a second printer....the Epson Workhorse 645 only costs about $80 and handles envelopes of all sizes very well.

Sounds like I need to reconsider what that ROI looks like as I haven't really thought about it from this angle.

I would really reconsider paying up 15k especially if it adversely affected my ability to borrow money for a while. 

Motivated sellers don't reconsider when they realize you're an investor who will make a profit on their property.

If you’re not willing to eat less and work more you may want to reconsider investing as a career choice. 

If I lived in another part of the country I might reconsider if the numbers would work.