Thanks The handwritten/sharpie style is the best option 

Unfortunately I don’t qualify for the free option and finding a contractor that actually wants to jump through the hoops for the permit waiver is another hurdle.

Many people in your position consider speaking with potential partners and co-signers.The co-op/condo market offers more options within your price range.

I based my insurance company for not covering it but later found out this isint something most insurance companies would cover.

However when we really got into it we decided to go north of the city for more affordable options.

Real Estate Agent, on MLS, negotiated with sellers based on Ribbon Cash Buyer program.

In my experience the basics for a functional RE based CRM are:Custom Fields for Data Objects (Leads, Prospects, Applications, Buildings, Units, etc...)A Screening Engine (background/credit checks, employment verification, etc)Online Rental Application (this should automatically run the application through screening)Ability to mass email/sms leads and tenants to provide informationSurveys/Inspection formsI've been building real estate CRM tools for years.

Cleveland offers a mix of affordable housing options and a solid rental market.

They're a small company based out of Ohio I believe and will work with you to build a custom CRM for you and your team. 

Check in with @Joseph Chiofalo he's Florida based and could be a good general resource.