Do I need to find one that specializes in what I am looking for...like self storage or warehouses or old building conversions? 

Consider looking for lenders who specialize in BRRRR strategies, as they might offer more favorable terms.

the majority of our off market inventory is within 3 months of being completed and we provide special incentives like investor pricing, rate buy downs, and property management discounts.Feel free to contact me directly if you want to talk about strategy or markets in Florida Best of luck

Two - In my due diligence, it looks like the only real option to make this unit legal is a special permit and variance, therefore, causing me to update the whole building with sprinklers, fire alarm, and meeting stretch code (certainly not enough meat on the bone for this route).  

I'm right near you in Gilberts and specialize in working with investors and house hackers, I've worked with dozens (maybe hundreds) of BP members on their financing over the years.

This in my experience is across the board with tenants, specially those who aren’t paying their rent on time.

One child is serious special needs.  

Speak with the Community Manager, or try to meet with one or more board members to gauge their attitudes on your investing ideas.Very Important:  check to see if there are any current or in-the-works special assessments. 

I'm not so much a DIY type when it comes to legal matters so I am looking for an experienced attorney who specializes in tax foreclosures - ideally in that county.

First off, I’d suggest connecting with a CPA who specializes in real estate and understands the specifics of Cleveland and Ohio state taxes.