Based on your assessment, it feels like the only way for you to buy something now is to make a compromise that you don't want to make or to get out over your skis a bit more than you'd like. 20 years from now, it won't make much of a difference whether you bought something today or two years from now. 

It is not really apples to apples, but generally speaking the more money invested the further ahead you will be eventually in the future, just because your compounding base is higher, regardless of where the money comes from - ie, 4 300k properties are 1.2 million on property, which is double the 600k property.

This is home for us, and our portfolio is based here.

@Yuan He, happy to connect with investor based in Nova scotia

Making decisions based on "rule of thumb" analysis isn't analysis, it's guessing. 

Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc. 

The GC should help you determine the scope of work and provide a list of materials based on your goals (e.g., rental vs. flip) and the property's target market.

If it were me, I’d double-check the furnace to cover all bases (maybe bring in a second opinion) and document everything.

They will tailor a program for you, based on their success with similar businesses.  

All in all - owning a place to rent to other people is a business, and business decisions need to be made based on that cold hard facts and not on an emotional basis, unless someone wants to quickly go out of business.