I am still working to purchase my first investment and when talking with the lender it seems like it could reduce the amount of work that they have to do and possibly portray a higher level of character and organization on my part.

Home under contract as retail flip but considering wholesaling.  3/2 with incredible character, 2 car garage, beautiful natural light from oversized windows in kitchen and dining, and much more.ARV - $365,000+Rehab estimate - $50,000 

Yet, there are still many old homes with abundant character for great prices. 

These are items that may boost your score some, but are red flags for financial character (potentially). 

I like larger properties, but I also like boutique properties with character especially if I can buy them at a big discount from a mom and pop with rents that are 10+ years behind the market...like the 6 unit I just bought on a creek in downtown Salem, OR.    

Withoutknowing the details I can not suggest which would be right to add on.Several you should pay attention to are:- Ordinance & Law: Provides additional building coverage to deal with rebuilding costIncreases due to changes in Zoning or Building laws- Personal Injury Liability: Libel, defamation of character, wrongful imprisonment, etc.

@Chad Gaither Anytime, NACA is a non profit that helps new owners purchase SFR or MF (1-4 units) with character based qualifications since it is geared toward low or moderate income folks.

We haven't tried reaching out for a mentor yet, but we have been offered many get rich quick real estate guru education programs for 30k buyins and promises of mastermind groups-- We all have unique experience professionally and personally, so i believe the different perspectives and character traits we carry could be a boon to someone without them.

You are correlating a person's character with their socioeconomic status.

All you other lovable characters are talking about what is "easy" and then giving your opinion, which is fine for debate class.