I researched online, it seems like most judgement will be granted in favor of landlord during the second trial (if provide all evidence such as our case).

I had a seller this year in a multiple offer situation reject a higher VA loan offer in favor of a lower, but otherwise very similar, conventional loan offer due to a very minor worry that the property wouldn't meet the VA minimum property standards.

My one struggle is that after watching plenty of videos reading the books and doing research, I feel like I don't know where to focus my new knowledge, and how to get that first deal in motion.

Are the odds in your favor?

I can say that the landlord tenant laws on the books in WI are more favorable to the owners opposed with Illinois where tenants receive much more leverage when it comes to eviction.  

I am also primiarily not a rental agent, so when I call it's normally a favor for a friends kid or something and I am just looking out for their best interest.

Ryan's got the down low on info from staking out a spot at the local coffee shop to make friends and find out where the area is gong.Do us a favor Ryan and give us an idea why Euclid is a good market for you?  

Do yourself a favor and get it appraised for $500 and get it sold ASAP.

If the cost of a duplex is already cheaper per unit than the cost of 2x SFRs (but, still currently out of your reach), do you think the ratio will go further in your favor, in 8 years? 

Rental markets are different, and the phoenix market favors appreciation, over monthly rents.