If values of real properties continue their long term increases, then owning more property even if it means having paid higher prices will turn out to be a winning strategy, provided the buyer is able to maintain ownership through periods of possible negative cash flow and or refinancing necessity. 

If the deal still looks decent in a worst case scenario you can feel more confident in going forward because many things things don't go as planned.

Is it worth keeping the house and increasing the rent to $1750 or should I sell in the market that we are in?

Yes, I’ve already used one DSCR loan for a property in Augusta and the higher closing costs are increasing my time between property purchases.

Know Tenant Rights: Oregon requires 90 days' notice for rent increases and enforces just-cause evictions.3.

The more experience you get, the smoother your process, the more confident you'll get in your contacts, and the better the terms you'll get from lenders.A few things to keep in mind for you as you go about your projects.1.

Accept a lower price due to the increased risk of the tenant 2.

Once updated, the building will provide modernized living spaces and support a significant rent increase, enhancing cash flow and property value.

These types of improvements increase your house hacking income. 

Quote from @Grayson Grzybowski: @Crystal SmithThank you for taking the time to provide your insight on the questions I have asked.For your introductory statement, I understand this is how debt should be used. 1) I have already went out of my way to ask for as high of a limit as I can just to have it on stand by. 2) I am trying to build value into our home to increase the equity faster so I can utilize it as leverage in time. 3) I have already reached out to a lot of different investors and have their terms & conditions at hand.