Milwaukee / Cleveland Property Management Companies and Advice

[Ryan Lynch]

Howdy folks!

I'm new to the site and thought this would be a good spot to start firing away questions and utilizing other's experience with good management companies and investing in certain areas. There are multiple questions I have and I'm sure I'll expose my lack of knowledge in asking them so feel free to point me to good learning resources as well. My goals with investing are to build passive income while being as hands off as possible, even at the cost of lower returns. My career path is one that I love, pays very well, and will also allow me to travel for almost no cost. I aim to retire early and have enough passive income and equity that I will have to make zero lifestyle changes after retirement.

For sake of efficiency I'll just bullet point my questions.

1.With long distance investing for a first investment (my area is basically impossible to make numbers work for rental investments) would it be worth the extra effort to buy and rehab foreclosures to rent or would it be wise to start simple and go with a ready to rent property for less returns?

2.When paying for a property management company will they have in-house maintenance cover small repairs and just send the owner a bill or do they typically have the owner (me) find handymen/contractors and deal with repairs myself?

3.I have funds enough to buy a few properties outright and not have interest to pay, but would it make more sense to take a loan and reap the benefits of having less capital into the investment?

3a.Is it too risky to dive in with 3+ properties immediately; should I start with 1 and see if real estate investing suits me?

4.What are your strategies for finding desirable neighborhoods for renters while not living in the city you're investing in?

5.How many properties warrants an LLC being formed instead of just owning them personally?

6.Even with the large amounts of "competition" in Cleveland and Milwaukee there seem to be quite a few properties with numbers that still work for me. Do you still think these markets are good places to start or could a beginner do better elsewhere?

7. Lastly, does anyone have any recommendations for good, honest property management companies in Cleveland or Milwaukee?

I'm certainly not expecting any one person to answer all of these questions so even if you only have an answer for one of them I would love the input!

Thanks for your time,

Ryan