After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.
It is common for a business owner who relies on machinery or equipment to have two business entities. One entity is an LLC that owns the assets. The other entity is an S corporation which leases the assets from the LLC to use in the business. This directly reduces the S Corp’s income, and might possibly reduce the amount of salary required to be paid by the business to the shareholders. Good news.
There’s a saying that the biggest opportunity for improvement is at the margin. Boiled down, this means that you can reap big rewards for minor adjustments in behavior. Instead of using a check, debit card or cash to pay for daily activities and big expenses, using a cashback credit card can earn you a sizeable return each year. One of my favorite cards, the Discover it will even double all of the cash back you earn the first year!
You must sacrifice the pleasures of today for the freedom you will earn tomorrow. In my 20s, I shared a studio with my best friend from high school and drove beater cars worth less than 10% of my annual gross income. I'd stay until after 7:30 p.m. at work in order to eat the free cafeteria food. International vacations were replaced with staycations since work already sent me overseas two to four times a year. Clothes were bought at thrift shops, of course.
I have only dabbled in drop-shipping before when I had an eCommerce platform 6 years ago or so. I think it is something that you could do on the side, but you would want to do in depth research on the industry you want to get into before setting up shop. It may be a little less passive up front, but over time you could take your hands off the wheel.