Like @Eric James said, if something is in decent shape, don’t waste money upgrading.If you have single pane windows, upgrading to dual pane vinyl frame is a worthy upgrade.

And I understand the financial strain.

Its a rural area, and the internet connection isnt strong so an additional TV will strain the wireless strength.2.

A new strain and Ukraine are risk factors to me but I don't know how to forecast when the straw will fall. 

The 2nd floor is always more challenging than the 1st floor but renting a lift gets you past the height issue.The main reasons I replace with standard sizes, I can check for water intrusion, I can insulate better, I can replace with dual pane, the windows are easier to open in an emergency, they are easier to replace in the future when a baseball goes through them, they look better and they increase value.

In other words, if it were a financial strain where I could *just* afford to enrol in a seminar, but my credit cards would be maxed out or I tapped into an equity line of credit, would this have been an advisable course of action?

Rehab time 6-8 weeks, 3 bed 2 bath ranch 1200 sq ft in Bristol PA needs full rehab.

Most single hung double pane windows I saw were in that range but do you use double hung double pane?

When individuals are stressed and overwhelmed, their communication style might be affected, leading to rushed conversations and strained relationships.

Replaced the 36X48 single pane with 36X36 double insulated windowsThankfully the side and rear windows were already 36X36 so they were a simple swap but we replaced all the trim work on these