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? I would advise getting turn key or near turn key. If you buy a property with tenants in place then you have immediate cash flow and can build some relationships and gain experience before taking on a project with more risk.
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? Some management companies require that you use their maintenance while others will provide maintenance but not require that use them. You don't want to be in a position to find people remotely, you might hit on a gem or you might have something that is less than stellar.
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? In general your COC returns are better when you finance, that being said you are reaping less total dollars in monthly return. If you have capital to do a few at a time then you can buy properties, season them (wait usually 6 months), refi and repeat. This will get you more properties, just make sure that you keep capital reserves to handle any unexpected events that come up. Also buying in cash will allow you to make more aggressive offers.
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? Its not necessarily risky to buy three properties but if REI is not for you then its just more work to back out. Selling houses isn't like selling a stock, it takes time and costs money so if you haven't held them for long or had much appreciation you could lose money.
4.What are your strategies for finding desirable neighborhoods for renters while not living in the city you're investing in? I invest locally so I have to pass on this question.
5.How many properties warrants an LLC being formed instead of just owning them personally? I would encourage buying in an LLC for even one property if you are a cash buyer. If you plan to take out a mortgage you will not qualify for all mortgages if the house is in the name of an LLC, and that applies to cash out refi's as well.
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? You can still find a good deal, you might just need to wait a bit longer to identify and get an offer accepted in current market conditions. I will caution you that many times numbers work on paper based on what you can see online but don't work out in reality. For example East Cleveland numbers always look great but the reality never lives up to the hype. You will hear lots of real estate professionals say that you make your money when you buy properties. Every market can make money and every market can do the opposite. Deferred maintenance can be very costly, getting a great property inspector and being willing to walk away from a property because there are too many items noted can save you from making more costly mistakes. I also would encourage you to call the inspector and ask them for their opinion, they usually won't put it in their report but they see so many properties and usually have a valuable gut feeling on whether its a good buy or not.