Any successful Landlords on here??

Issue 1- Be prepared to divorce yourself from the property emotionally. It will no longer be a "home", but a rental "house", and business asset.

Issue 2- Get/write a GOOD lease. I do my own, but it takes lots of homework, and should always be a "work in progress".

* most states have a "holdover" provision, where you can charge double rent when a tenant stays past the end of the lease (which you can terminate for just cause, including non-payment), however, usually it's not worth a lawsuit unless there are thousands and thousands of dollars involved. You still have layer fees and may only get a $100 garnishment or worse such as paying a collection agency. Most states have a 3 day/15 day notice and 30 day eviction law. Send notices promptly. It's easy to lose months.

Issue 3- location, location, location. Ours is in a position between two major cities, and near the connecting highway. It almost rents it's self. Not so lots of other properties.

Issue 4- Target market. The "ideal" rental house is about 1200 sq/ft and under $1000/month (at least around here), any less rent and the quality of tenant declines, any more and the "nit-pick" factor increases ("for 1200 a month the knobs had BETTER match, and the irrigation better work, not to mention that big driveway crack and those weeds..." -is something I imagine hearing).

* I'd also be leery of renting the type of property you have for most of the reasons listed already. Another issue with trying to rent an "estate" is that you're likely to have to run empty for longer periods of time betwen tenants.

Issue 5- Management. I agree it's better to do it yourself, if you can. If you can't, perhaps rental real estate is not for you (unless you're seasoned and can micro-manage, but then what's the point?). For tax purposes you have to prove "material participation" or there are some "passive income" issues to deal with.

Issue 6- Dealing with being behind- All of your expenses occur this year. All of the tax based recovery of those expenses will happen next year. Deal with it, and plan ahead.
Expect property tax and insurance to go up by 15% per year. That can be thousands out of pocket, albeit temporarily.

Issue 7- Do your own repairs- We do as much as we can, especially when we have to "reset" between tenants. It's real easy to kill the whole year's profit by hiring out work. Sure you get some or all of it back, but you better get/keep receipts and remember, you only get it back in April, no matter when you spend it. We also set clear guidelines for what kinds of maintenance we expect/encourage the tenants to do (like light bulbs, and yard work), and what they should call us for.

Issue 8- Bad tenants- Just part of the business. Get used to it. We've had two leave under not so great circumstances, and one that was terrible. Each time, you learn something that helps with the next time. OTOH, we've had some that were GREAT. One built a paver deck (with our blessing) and the current ones painted the entry way and installed a new light fixture (again, with our blessing).

I'm sure there's more in my head, but those are what came to the surface.
My wife and I started with zero experience, and are now in year seven.
That experience was a big factor in my decision to buy the mini-warehouse buildings (now in year three), and we are currently looking for another house in the same neighborhood.
For me, the time we spend on the rentals (both the house and the warehouse) are well worth the few extra grand we get each year. I figure we spend about a week per year (a couple hours here...) on the house. Two if we have a tenant change, and I spend about a week per quarter on the warehouse (of course I'm also there working on my cars quite a bit).