These options would still keep your costs down while offering practical benefits that could attract a larger demographic of renters.Starting with one of these simpler conversions also gives you the flexibility to explore more ambitious plans down the road once you have a better understanding of the property's potential and your own budget constraints.Hope this helps clarify the options.

One pitfall can be using Hard / Private Money to stretch into larger deals.

But if it's much larger than that, maybe you consider selling and doing a 1031.

My property manager then sent another technician who said the gutters need to be cleaned and recommended installing leaf guards around the entire duplex, along with larger downspouts and overflow guards, for a total of $3,013.

If you're looking for larger commercial multifamily (5+ units) then you may have better luck on the commercial sites, crexi and loopnet.

I like leveraging money when in appreciating markets because of the ability to see much larger returns on your money invested. 

When everything has to be in different "apps" to get stuff done, you introduce a ton of clicks into your repetitive tasks...and that gets annoying fast!

It may be a situation where you need to either learn more accounting or hire this task out.No other software is going to help you as the same mistakes you made in QuickBooks will be the same mistakes you make in any other software.  

You're taking on the bulk of the work and management responsibilities, which justifies a larger share.

This can help you cover your mortgage while you build equity and gain more experience managing multiple tenants and building out better systems and processes if you do decide you want to pursue larger properties.