With the goal of acquiring my first small mf by 2020 ( 4-8 units, out of state ), I am honing my market analysis skills. 

If you have experience in real estate photography, why not combine your skill and your money toward someone else's deal?

Trade time and skills for exposure to projects.

Where do you have skills, local knowledge, time or something else? 

She has also developed a positive relationship with him which has led to discussions with him sharing his financial situation (which is not terribly good due to the poor estimation skills mentioned before). 

With your skills and contacts in the industry you can certainly find some value-add opportunities.

Developing my skills and knowledge of real estate in general.

Take a course and implement immediately what skill you've learned before you move to the next thing.4) Become an expert at one thing.

Of course this depends on your landlording skills. 

Professionals master one major skill at a time.