In my experience, your level of wealth that you can handle is based on your mindset.

They didn't pay for it, so they don't take care of it like an owner.Before you make assumptions about costs based on a seller's contribution to improvements, find out what they improved? 

We consulted with a designer once, but saw it as no value based on what we had already done ourselves.

So you went based on pricing.3.

Here’s a thought:Step back and evaluate which properties, if any, are truly worth keeping based on current performance and future potential.

Another variable in the amount of rent that a Section 8 tenant can pay is HUD limits their rent payment based on the amount of their income. 

I think it is fair to say that there is somewhat of a tradeoff between markets that provide positive cash flow on day one and relatively high appreciation-based markets.

The assessor has to assess it based on other similar properties with their SEV.

I recommend finding a US-based bookkeeper who specializes in real estate and doesn't have too much on their plate.

That affects your loan amount and then principal & interest payment.2) Estimate rents based on recent rental comps3) Account for all operating expenses such as property taxes, insurance, repairs & maintenance (landscaping, snow removal, cleaning etc), property management (if applicable), vacancy, utilities (what does the tenant pay vs what you would pay?)