Even with the manager, in mine, I'm thinking about and doing more in the STR than they ones I actively manage.

Fastest way to learn is by networking with people who are actively doing what you want to be doing in the future 

.- Get a list of active properties in a zipcode with filters (number of bedrooms, bathrooms, price etc)

A month back he asked me to add his brother and his wife to the lease and I asked him that they need to go through criminal and other checks that we went through.

I am actively looking to expand throughout the Caribbean. 

@Andres Felipe Alba Hernandez Yes, neighborhood covenants can sometimes restrict certain activities, including short-term rentals (STRs) or renting out parts of a home, even in areas without a Homeowners Association (HOA).

Greenfield is a growing area, and being in a golf course neighborhood across two lots adds a ton of value to your options.I’d recommend starting by connecting with local investor groups or meetups in Indianapolis—Facebook groups or here on BiggerPockets are solid places to find people actively working in that market.

Most banks allow you to export the full year of activity to excel.If you are not comfortable using excel - you should reach out to your accountant if he/she has a bookkeeper on staff and how much it would cost them to do your books.It may be cheaper overall for your accountant to do it if you just need the books to be done once a year instead of on a monthly basis.Furthermore, this saves you from having to pay for the software.

I know this may not seem possible, and probably not the answer you were looking for, but it would be worth partnering with another active investor, bringing in a passive investor(s), or even waiting until you have enough capital to deploy into the right deal. 

Active real estate investors who can't get comfortable not being in the driver's seat, people who just don't like real estate as an investment, those who can't get comfortable with the risks, those who just don't understand syndicate investments, those who have heard bad things about this type of investing from others, and people who have invested in syndicates and experienced bad results.