Even if they do not, it’s not your legal responsibility.Long version: It actually depends on your method of payment, and it’s not always clear.Credit card payments: clearly not you problem, no 1099s needed.Zelle payments: you DO need to send 1099s for Zelle payments.PayPal, Venmo and Cash App payments: this is where it gets tricky.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

This is assuming the way you notified the tenants of the new rent was considered legal notice in your market. 

Unless a property has a non-conforming use permit (NUC), there are only 4 areas on O'ahu that you can legally do STRS.  

I don't necessarily need the standard features of pm software, such as rent collection, bookkeeping and maintenance requests, though that could help; but do need a clearinghouse of important information, such as leases, legal docs and other information; maintenance vendors I use; maintenance history; and some kind of tracking system, where I can record the various current projects I'm working on within the business.

Hey Santosh,As of right now you're extremely exposed regarding insurance and I'm going to assume legally as well.If the home isn't registered as a legal multi-family with the town that's something you'll have to correct ASAP and make sure the home is up to code.Insurance wise as soon as they find out what you're doing they'll cancel you as the risk has changed from a single family owner occupied home to a multi family owner occupied home.

Quote from @Michael Smythe: @Sean Gallagher legally you are correct, but many tenants do NOT know this.We take over properties all the time and close 80% of existing tenants sign a lease with us.True! 

Weeks later, it was communicated to us that the underwriter wouldn’t accept the ones signed by only one of us – legally binding for LLCs – and required we send amended copies of leases signed by both of us.

Time is money and I prefer spending my time with my fam and friends instead of problem tenants and legal cases. 

I prefer graduate students whenever possible because they don't have time for partying, are of legal age anyway, and generally tend to be by themselves or with a partner so it's more like renting to a couple.