The main problem with negative cashflow properties is this. 

A grand negative cash flow is not the issue.

If both houses were sold in 2024 then the loss will negate the profit from my understanding.

This creates a large negative equity position.  

@Makani Donaldson it all depends on your investment goals.If you buy a Class A rental, it'll usually have negative cashflow, which will be hopefully offset with appreciation and better tenants.If you buy a CLass C or D rental, it should have pretty good cashflow because you may not realize much in appreciation and you'll have a lot more problems finding good tenants.

I wouldn't consider it a heavy negative unless the street is super tight and parking is hard to come by or if the street is very steep/busy.The more desirable dense city neighborhoods it's almost kind of expected and off street parking would be considered a luxury rather than a necessity.If you get out into the suburbs I would say it's more of a big deal since more rentals have off street parking or a garage there.

There are people here who have no problem losing hundreds to thousands in negative cash flow monthly.

Yes you can find properties which you will be able to purchase, but ROI will be near zero or negative. 

For this deal to work under those conditions, the purchase price would need to be closer to $179k.With your original assumptions 249k, the deal is marginally acceptable but not great, given the negative cash flow in the early years.

You can usually get a lender to go 85% of cost or 70% of the As Completed Value for such a project.