That may increase your cost or limit the coverage you can get.The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policy.

.- Can't see a Senior-Only complex allowing Short-Term-Rentals (STR).If so, SELL.2) What is the history of Association Fee increases and how well capitalized is the Association for future repairs?

My plan for this year is improve my credit, get my real estate license (to increase my income on top of my W-2), possibly career transition into the property management space (to learn more), and save as much as possible and learn as much as I can.I’d love to house hack close to home but my area is so expensive it seems like it’d be close to impossible. 

This is usually done to increase your rental income but it comes with a price as you are finding out.  

By the 3rd or 4th year if they aren't the same or have increased we all prob will have bigger problems

As they see their money is safe and you're succeeding with your plans, they'll usually ask to increase the amount of money they loan to you.

Increase income, decrease DTI, and buy a home (i.e., get a higher paying job, work two jobs, go to trade school, get a higher paying degree, live in affordable area, etc...these are things that most of us did).

If they have, you extend that time to 6 months from date of death.On top of that, every month you delay buying the house, the loan balance is going to increase. 

. - In the event that you do get a deal, that you do not violate the intent or letter of an increasing number of anti-wholesaling laws, and that you actually receive an assignment fee, you will walk away thinking that your role is over.

It's not necessarily that the value of your house is increasing.