Having a good plumber, electrician, etc that will work for a little less to supplement their income is great.

A possible/proposed solution might to be supplement the existing posts where there are issues, and add new posts where there may be any risk of moment forces causing failure.As long as there's not acute damage due to water, termites, etc of your joists I think this would be a reasonable approach to at least explore.Most jurisdictions do look for opportunities to ensure that when a contractor touches something they replace MOST or ALL of the system. 

I'm open to investing in different regions of the country, and using that rental income to supplement renting personally in SD.

I look at my ROTH accounts as supplements to that, but I don't plan to withdraw my contributions any time soon. 

You must be prepared to supplement tenant's rent till you are ready to cash out.In your area investors develop very high risk tolerance and move forward hoping to get out before th emarkets change.

I love dogs, (cats, too, but I'm allergic),  I do my best to accommodate them,  but I won't be tolerating B.S.ADA rules say RELIABLE documentation.....

Could I use my LLC that the properties are in as a year's worth of income, supplemented with my current personal income?

Some questions I have are I have a new child, so I am not able to save much from my w2 job and looking to do a side hustle to supplement.

My goals are for now to supplement my income, but I want to be in a position in 5 years to be able to quit my day job and be a full time investor.

You can read their quarterly reports but they usually have even better information on their websites as 'supplements' to their earnings calls.